Organic sulfur compounds and use thereof

ABSTRACT

A compound given by the formula (I): 
     
       
         
         
             
             
         
       
     
     has an excellent controlling activity against noxious arthropods.

TECHNICAL FIELD

The present invention relates to organic sulfur compounds and noxiousarthropod controlling use thereof.

BACKGROUND ART

Many arthropods controlling agents have been developed and practicallyused.

DISCLOSURE OF INVENTION

The present invention provides novel compounds having an excellentactivity against noxious arthropods.

Namely, the present invention provides an organic sulfur compound givenby the following formula [I]:

whereinR¹ represents a C3-C6 fluoroalkyl group,R² represents a cyano group, a group represented by C(═O)R⁵ or a grouprepresented by C(═S)R⁶,R³ represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group,R⁴ represents a C1-C5 fluoroalkyl group,R⁵ and R⁶ independently represent a C1-C4 alkoxy group, an amino groupoptionally substituted by one or two C1-C4 alkyl group(s) or a C2-C5cyclic amino group,n represents 0, 1 or 2;(may refer as the present compound, hereinafter), a noxious arthropodcontrolling agent comprising the present compound and an inert carrierand a method for controlling noxious arthropods applying an effectiveamount of the present compound to noxious arthropods or at a habitat ofnoxious arthropods.

MODE OF CARRYING OUT THE INVENTION

In the present invention, the mention of C1-C4 and the like means thetotal number of carbon atoms which comprises each substituents. And inthe present invention, the mention of fluoroalkyl group means an alkylgroup substituted one or more fluorine atom(s) are substituted at carbonatoms.

Examples of C3-C6 fluoroalkyl group represented by R¹ in the formula (I)includes

C3 fluoroalkyl group such as 2-fluoropropyl group, 2,2-difluoropropylgroup, 3-fluoropropyl group, 3,3-difluoropropyl group,3,3,3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group,2,2,3,3-tetrafluoropropyl group and2,2,2-trifluoro-(1-trifluoromethyl)ethyl group; C4 fluoroalkyl groupsuch as 2-fluorobutyl group, 2,2-difluorobutyl group, 3-fluorobutylgroup, 3,3-difluorobutyl group, 4-fluorobutyl group, 4,4-difluorobutylgroup, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group,2,2,3,4,4-pentafluorobutyl group and 2,2,3,3,4,4,4-heptafluorobutylgroup;C5 fluoroalkyl group such as 2-fluoropentyl group, 2,2-difluoropentylgroup, 3-fluoropentyl group, 3,3-difluoropentyl group, 4-fluoropentylgroup, 4,4-difluoropentyl group, 5-fluoropentyl group,5,5-difluoropentyl group, 5,5,5-trifluoropentyl group,4,4,5,5,5-pentafluoropentyl group, 3,3,4,4,5,5,5-heptafluoropentylgroup, 2,2,3,3,4,4,5,5-octafluoropentyl group and2,2,3,3,4,4,5,5,5-nonafluoropentyl group;C6 fluoroalkyl group such as 2-fluorohexyl group, 2,2-difluorohexylgroup, 3-fluorohexyl group, 3,3-difluorohexyl group, 4-fluorohexylgroup, 4,4-difluorohexyl group, 5-fluorohexyl group, 5,5-difluorohexylgroup, 6-fluorohexyl group, 6,6-difluorohexyl group,6,6,6-trifluorohexyl group, 5,5,6,6,6-pentafluorohexyl group,4,4,5,5,6,6,6-heptafluorohexyl group, 3,3,4,4,5,5,6,6,6-nonafluorohexylgroup and 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl group.

Examples of C1-C5 fluoroalkyl group represented by R⁴ in the formula (I)includes

C1-C2 fluoroalkyl group such as fluoromethyl group, difluoromethylgroup, trifluoromethyl group, 1-fluoroethyl group, 2-fluoroethyl group,1,1-difluoroethyl group, 2,2-fluoroethyl group, 2,2,2-trifluoroethylgroup and 1,1,2,2,2-pentafluoroethyl group;C3 fluoroalkyl group such as 1-fluoropropyl group, 1,1-difluoropropylgroup, 2-fluoropropyl group, 2,2-difluoropropyl group, 3-fluoropropylgroup, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group,1,1,2,2,3,3,3-heptafluoropropyl group, 2,2,3,3,3-pentafluoropropylgroup, 2,2,2-trifluoro-(1-trifluoromethyl)ethyl group,1,2,2,2-tetrafluoro-(1-trifluoromethyl)ethyl group and2,2,3,3-tetrafluoropropyl group;C4 fluoroalkyl group such as 1-fluorobutyl group, 1,1-difluorobutylgroup, 2-fluorobutyl group, 2,2-difluorobutyl group, 3-fluorobutylgroup, 3,3-difluorobutyl group, 4-fluorobutyl group, 4,4-difluorobutylgroup, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group,2,2,3,4,4-pentafluorobutyl group and 2,2,3,3,4,4,4-heptafluorobutylgroup;C5 fluoroalkyl group such as 1-fluoropentyl group, 1,1-difluoropentylgroup, 2-fluoropentyl group, 2,2-difluoropentyl group, 3-fluoropentylgroup, 3,3-difluoropentyl group, 4-fluoropentyl group,4,4-difluoropentyl group, 5-fluoropentyl group, 5,5-difluoropentylgroup, 5,5,5-trifluoropentyl group, 4,4,5,5,5-pentafluoropentyl group,3,3,4,4,5,5,5-heptafluoropentyl group, 2,2,3,3,4,4,5,5-octafluoropentylgroup and 2,2,3,3,4,4,5,5,5-nonafluoropentyl group.

Examples of C1-C4 alkyl group represented by R³ in the formula (I)includes methyl group, ethyl group, propyl group, isopropyl group, butylgroup, isobutyl group and tert-butyl group.

Examples of C1-C4 alkoxy group represented by R⁵ and R⁶ in the formula(I) includes methoxy group, ethoxy group, propoxy group, isopropoxygroup, butoxy group, isobutoxy group and tert-butoxy group.

Examples of amino group optionally substituted by one or two C1-C4 alkylgroup(s) represented by R⁵ and R⁶ in the formula (I) includes aminogroup, methylamino group, ethylamino group, propylamino group,2-propylamino group, butylamino group, isobutylamino group,tert-butylamino group and dimethylamino group.

Examples of C2-C5 cyclic amino group represented by R⁵ and R⁶ in theformula (I) includes 1-aziridino group, 1-azetidinyl group,1-pyrrolizinyl group and 1-piperidino group.

Examples of the embodiment of the present compounds include asfollowing:

An organic sulfur compound wherein n is 2 in the formula (I);An organic sulfur compound wherein R² is a cyano group or a grouprepresented by C(═O)R⁵ in the formula (I);An organic sulfur compound wherein R² is a cyano group in the formula(I);An organic sulfur compound wherein R² is a group represented by C(═O)R⁵and R⁵ is an amino group optionally substituted by one or two C1-C4alkyl group(s) in the formula (I);An organic sulfur compound wherein R² is a group represented by C(═O)R⁵and R⁵ is an amino group in the formula (I);An organic sulfur compound wherein 3 is a halogen atom in the formula(I);An organic sulfur compound wherein R³ is a fluorine atom or a chlorineatom in the formula (I);An organic sulfur compound wherein R⁴ is a C1-C3 fluoroalkyl group inthe formula (I);An organic sulfur compound wherein R⁴ is a trifluoromethyl group in theformula (I);An organic sulfur compound wherein R⁴ is a 1,1,2,2,2-pentafluoroethylgroup in the formula (I);An organic sulfur compound wherein R⁴ is a1,1,2,2,3,3,3-heptafluoropropyl group in the formula (I);An organic sulfur compound wherein n is 2 and R⁴ is a C1-C3 fluoroalkylgroup in the formula (I);An organic sulfur compound wherein n is 2 and R⁴ is a trifluoromethylgroup in the formula (I);An organic sulfur compound wherein n is 2 and R⁴ is a1,1,2,2,2-pentafluoroethyl group in the formula (I);An organic sulfur compound wherein n is 2 and R⁴ is a1,1,2,2,3,3,3-heptafluoropropyl group in the formula (I);An organic sulfur compound wherein n is 2 and R² is a cyano group or agroup represented by C(═O)R⁵ in the formula (I);An organic sulfur compound wherein n is 2 and R² is a cyano group in theformula (I);An organic sulfur compound wherein n is 2, R² is a group represented byC(═O)R⁵ and R⁵ is an amino group optionally substituted by one or twoC1-C4 alkyl group(s) in the formula (I);An organic sulfur compound wherein n is 2, R² is a group represented byC(═O)R⁵ and R⁵ is an amino group in the formula (I);An organic sulfur compound wherein n is 2 and R³ is a halogen atom inthe formula (I);An organic sulfur compound wherein n is 2 and R³ is a fluorine atom or achlorine atom in the formula (I);An organic sulfur compound wherein R² is a cyano group or a grouprepresented by C(═O)R⁵ and R³ is a halogen atom in the formula (I);An organic sulfur compound wherein R² is a cyano group and R³ is ahalogen atom in the formula (I);An organic sulfur compound wherein R² is a group represented by C(═O)R⁵,R⁵ is an amino group optionally substituted by one or two C1-C4 alkylgroup(s) and R³ is a halogen atom in the formula (I);An organic sulfur compound wherein R² is a group represented by C(═O)R⁵,R⁵ is an amino group and R³ is a halogen atom in the formula (I);An organic sulfur compound wherein R² is a cyano group or a grouprepresented by C(═O)R⁵ and R³ is a fluorine atom or a chlorine atom inthe formula (I);An organic sulfur compound wherein R² is a cyano group and R³ is afluorine atom or a chlorine atom in the formula (I);An organic sulfur compound wherein R² is a group represented by C(═O)R⁵,R⁵ is an amino group optionally substituted by one or two C1-C4 alkylgroup(s) and R³ is a fluorine atom or a chlorine atom in the formula(I);An organic sulfur compound wherein R² is a group represented by C(═O)R⁵,R⁵ is an amino group and R³ is a fluorine atom or a chlorine atom in theformula (I);An organic sulfur compound wherein n is 2, R² is a cyano group or agroup represented by C(═O)R⁵ and R³ is a halogen atom in the formula(I);An organic sulfur compound wherein n is 2, R² is a cyano group and R³ isa halogen atom in the formula (I);An organic sulfur compound wherein n is 2, R² is a group represented byC(═O)R⁵, R⁵ is an amino group optionally substituted by one or two C1-C4alkyl group(s) and R³ is a halogen atom in the formula (I);An organic sulfur compound wherein n is 2, R² is a group represented byC(O)R⁵, R⁵ is an amino group and R³ is a halogen atom in the formula(I);An organic sulfur compound wherein n is 2, R² is a cyano group or agroup represented by C(═O)R⁵ and R³ is a fluorine atom or a chlorineatom in the formula (I);An organic sulfur compound wherein n is 2, R² is a cyano group and R³ isa fluorine atom or a chlorine atom in the formula (I);An organic sulfur compound wherein n is 2, R² is a group represented byC(═O)R⁵, R⁵ is an amino group optionally substituted by one or two C1-C4alkyl group(s) and R³ is a fluorine atom or a chlorine atom in theformula (I);An organic sulfur compound wherein n is 2, R² is a group represented byC(═O)R⁵, R⁵ is an amino group and R³ is a fluorine atom or a chlorineatom in the formula (I);An organic sulfur compound wherein R³ is a hydrogen atom or a halogenatom in the formula (I);An organic sulfur compound wherein R³ is a hydrogen atom or a C1-C4alkyl group in the formula (I);An organic sulfur compound wherein R³ is a halogen atom or a C1-C4 alkylgroup in the formula (I);An organic sulfur compound wherein R³ is a hydrogen atom or a halogenatom and R⁴ is a C1-C3 fluoroalkyl group in the formula (I);An organic sulfur compound wherein R³ is a hydrogen atom or a C1-C4alkyl group and R⁴ is a C1-C3 fluoroalkyl group in the formula (I);An organic sulfur compound wherein R³ is a halogen atom or a C1-C4 alkylgroup and R⁴ is a C1-C3 fluoroalkyl group in the formula (I).

Next, production method of the present compound is described.

For example, the present compound can be produced by following(Production Method 1) to (Production Method 12).

(Production Method 1)

The compound (I-2) which R³ is C1-C4 alkyl group in the present compoundcan be produced, for example, by making react the following compound (a)and the compound (I-1).

wherein R¹, R², R⁴ and n have the same meaning as described above, R³¹represents a C1-C4 alkyl group, X represents a leaving group such as achlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxygroup, a p-toluenesulfonyloxy group and trifluoromethanesulfonyloxygroup.

The reaction is usually carried out in a solvent and in the presence ofa base.

The solvent used for the reaction includes, for example, acid amidessuch as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, water and the mixturethereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate and the like, alkaline metal alkoxides such as sodiummethoxide, potassium tert-butoxide and the like, alkaline metal amidessuch as lithium diisopropylamide and the like and organic bases such astriethylamine, 1,4-diazabicyclo[2.2.2]octane,1,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of base usedfor the reaction is usually 1 to 10 moles based on 1 mole of thecompound (I-1).

The amount of the compound (a) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (I-1).

The reaction temperature is usually in the range of −100 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (I-2) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (I-2) may be purified, ifnecessary, by chromatography, recrystallization and the like.

(Production Method 2)

The compound (I-3) which R³ is a hydrogen atom or a C1-C4 alkyl group inthe present compound can be produced, for example, by making react thefollowing compound (c) and the compound (d).

wherein R¹, R², R⁴, n and X have the same meaning as described above,R³⁻² represents a hydrogen atom or a C1-C4 alkyl group.

The reaction is usually carried out in a solvent and in the presence ofa base.

The solvent used for the reaction includes, for example, acid amidessuch as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, water and the mixturethereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate and the like, alkaline metal alkoxides such as sodiummethoxide, potassium tert-butoxide and the like, alkaline metal amidessuch as lithium diisopropylamide and the like and organic bases such astriethylamine, 1,4-diazabicyclo[2.2.2]octane,1,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of base usedfor the reaction is usually 1 to 10 moles based on 1 mole of thecompound (d).

The amount of the compound (c) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (d).

The reaction temperature is usually in the range of −100 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (I-3) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (I-3) may be purified, ifnecessary, by chromatography, recrystallization and the like.

The compound (I-4) which R³ is a halogen atom in the present compoundcan be produced, for example, according to (Production Method 3) or(Production Method 4).

(Production Method 3)

The production method by making react the compound (I-1) andhalogenating agent (e) in the presence of a base.

wherein R¹, R², R⁴ and n have the same meaning as described above, R³⁻³represents a halogen atom.

The reaction is usually carried out in a solvent and in the presence ofa base.

The solvent used for the reaction includes, for example, acid amidessuch as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, water and the mixturethereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate and the like, alkaline metal alkoxides such as sodiummethoxide, potassium tert-butoxide and the like, alkaline metal amidessuch as lithium diisopropylamide and the like and organic bases such astriethylamine, 1,4-diazabicyclo[2.2.2]octane,1,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of base usedfor the reaction is usually 1 to 10 moles based on 1 mole of thecompound (I-1).

The halogenating agent (e) used for the reaction includes, for example,halogenated hydrocarbons such as carbontetrachloride, hexachloroethaneand the like, halogens such as fluorine, chlorine, bromine and iodine,halogenated succinimide such as N-chloro succinimide, N-bromosuccinimide, N-iodo succinimide and the like, N-fluoropyridinium saltsuch as 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate,1,1′-difluoro-2,2′-bipyridinium bistetrafluoroborate and the like,copper halide such as copper(II) chloride, copper(II) bromide and thelike.

The amount of halogenating agent (e) used for the reaction is usually 1to 10 moles based on 1 mole of the compound (I-1).

The reaction temperature is usually in the range of −100 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (I-4) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (I-4) may be purified, ifnecessary, by chromatography, recrystallization and the like.

(Production Method 4)

The production method by making react the compound (I-1) andhalogenating agent (f).

wherein R¹, R², R⁴, R³⁻³ and n have the same meaning as described above.

The reaction is carried out without a solvent or in a solvent.

The solvent used for the reaction includes, for example, halogenatedhydrocarbons such as chloroform, carbontetrachloride,1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbonssuch as toluene, xylene and the like, aliphatic nitrites such asacetonitrile, propionitrile and the like, aliphatic carboxylic acidssuch as acetic acid, carbon disulfide, water and the mixture thereof.

The halogenating agent (f) used for the reaction includes, for example,halogens such as fluorine, chlorine, bromine and iodine, hydrogenhalides such as hydrogen fluoride, hydrogen chloride, hydrogen bromideand hydrogen iodide, halogenated sulfur compound such as thionylchloride, thionyl bromide, sulfuryl chloride and the like, halogenatedphosphorus compound such as phosphorus trichloride, phosphorustribromide, phosphorus pentachloride, phosphorus oxychloride and thelike.

The amount of halogenating agent (f) used for the reaction is usually 1to 10 moles based on 1 mole of the compound (I-1).

The reaction temperature is usually in the range of −100 to 200° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (I-4) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (I-4) may be purified, ifnecessary, by chromatography, recrystallization and the like.

The compound (I-5) which R² is a group represented by C(═O)R⁵ and R⁵ isa C1-C4 alkoxy group, an amino group optionally substituted by one ortwo C1-C4 alkyl group(s) or a C2-C5 cyclic amino group in the presentcompound can be produced, for example, according to (Production Method5) or (Production Method 6).

(Production Method 5)

wherein R¹, R³, R⁴, R⁵ and n have the same meaning as described above, Zrepresents a halogen atom.

(Step 5-1)

The compound (i) can be produced by making react the compound (g) andhalogenating agent (h).The reaction is carried out without a solvent or in a solvent.

The solvent used for the reaction includes, for example, halogenatedhydrocarbons such as chloroform, dichloromethane, 1,2-dichloroethane,chlorobenzene and the like, aromatic hydrocarbons such as toluene,xylene and the like.

The halogenating agent (h) used for the reaction includes, for example,oxalyl chloride, thionyl chloride, thionyl bromide, phosphorustrichloride, phosphorus tribromide and phosphorus pentachloride. Theamount of halogenating agent (h) used for the reaction is usually 1 moleto excess based on 1 mole of the compound (g).

The reaction temperature is usually in the range of −20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (i) can be isolated bysubjecting a treatment such as concentrating the reaction mixture. Theisolated compound (i) may be purified by distillation and the like.

(Step 5-2)

The reaction is usually carried out in a solvent and in the presence ofa base.

The solvent used for the reaction includes, for example, acid amidessuch as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, water and the mixturethereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate and the like and organic bases such as triethylamine,1,4-diazabicyclo[2.2.2]octane, 1,8-diazabicyclo[5.4.0]-7-undecene andthe like. The amount of base used for the reaction is usually 1 to 10moles based on 1 mole of the compound (i).

The amount of the compound (j) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (i).

The reaction temperature is usually in the range of −20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (I-5) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (I-5) may be purified, ifnecessary, by chromatography, recrystallization and the like.

(Production Method 6)

The production method by making react the compound (g) and the compound(j).

wherein R¹, R³, R⁴, R⁵ and n have the same meaning as described above.

The reaction is usually carried out in a solvent and in the presence ofa condensing agent.

The solvent used for the reaction includes, for example, ethers such asdiethyl ether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like andaromatic hydrocarbons such as toluene, xylene and the like.

The condensing agent used for the reaction includes, for example,dicyclohexylcarbodiimide,N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide, carbonyldiimidazole andthe like.

The amount of condensing agent used for the reaction is usually 1 to 10moles based on 1 mole of the compound (g).

The amount of the compound (j) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (q).

The reaction temperature is usually in the range of −20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (I-5) can be isolated bysubjecting a treatment such as pouring the reaction mixture into water,extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (I-5) may be purified, ifnecessary, by chromatography, recrystallization and the like.

(Production Method 7)

The compound (I-1) which R³ is a hydrogen atom in the present compoundcan be produced, for example, by making react the compound (c) and thecompound (k).

wherein R¹, R², R⁴, X and n have the same meaning as described above.

The reaction is usually carried out in a solvent and in the presence ofa base.

The solvent used for the reaction includes, for example, acid amidessuch as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, water and the mixturethereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate and the like, alkali metal alkoxides such as sodium methoxide,potassium tert-butoxide and the like, alkali metal amides such aslithium diisopropyl amide and the like and organic bases such astriethylamine, 1,4-diazabicyclo[2.2.2]octane,1,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of base usedfor the reaction is usually 1 to 10 moles based on 1 mole of thecompound (k).

The amount of the compound (c) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (k).

The reaction temperature is usually in the range of −100 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (I-1) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (I-1) may be purified, ifnecessary, by chromatography, recrystallization and the like.

(Production Method 8)

The compound (I-8) which R² is a group represented by C(═O)R⁵, R⁵ is anamino group optionally substituted by one or two C1-C4 alkyl group(s) ora C2-C5 cyclic amino group and n is 2 in the present compound can alsobe produced by making the compound (I-7), which R² is a grouprepresented by C(═O)R⁵, R⁵ is a C1-C4 alkoxy group and n is 2, reactwith the compound (p).

wherein R¹, R³ and R⁴ have the same meaning as described above, R⁵⁻¹represents a C1-C4 alkoxy group, R⁵⁻² represents an amino groupoptionally substituted by one or two C1-C4 alkyl group(s) or a C2-C5cyclic amino group.

The reaction is usually carried out in a solvent.

The solvent used for the reaction includes, for example, ethers such asdiethyl ether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like.

The amount of the compound (p) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (I-7).

The reaction temperature is usually in the range of −20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (I-8) can be isolated bysubjecting a post-treatment such as of concentrating the reactionmixture. The isolated compound (I-8) may also be purified, if necessary,by chromatography, recrystallization and the like.

(Production Method 9)

The compound (I-9) which R² is a group represented by C(═S)R⁵ in thepresent compound can also be produced by making the compound (I-5) whichR² is a group represented by C(═O)R⁵ react with the sulfurnating agent(q).

wherein R¹, R³, R⁴, R⁵ and n have the same meaning as described above.

The reaction is usually carried out in a solvent.

The solvent used for the reaction includes, for example, halogenatedhydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene andthe like, aromatic hydrocarbons such as toluene, xylene and the like.

The sulfurnating agent (q) used for the reaction includes, for example,inorganic sulfur compounds such as hydrogen sulfide, organic sulfurcompounds such as phosphorus pentasulfide and the like and2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide andthe like.

The amount of the sulfurnating agent (q) used for the reaction isusually 0.5 to 10 moles based on 1 mole of the compound (I-5).

The reaction temperature is usually in the range of 0 to 250° C. and thereaction period is usually 1 to 72 hours.

After the reaction has finished, the compound (I-9) can be isolated bysubjecting a post-treatment such as of concentrating the reactionmixture. The isolated compound (I-9) may be purified, if necessary, bychromatography, recrystallization and the like.

The compound (I-10) which n is 0 in the present compound can beproduced, for example, by according to (Production Method 10) or(Production Method 11).

(Production Method 10)

The production method by making react the compound (r) and the compound(m).

wherein R¹, R², R³⁻², R⁴ and X have the same meaning as described above.

The reaction is usually carried out in a solvent and in the presence ofa base.

The solvent used for the reaction includes, for example, acid amidessuch as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, water and the mixturethereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate and the like, alkali metal alkoxides such as sodium methoxide,potassium tert-butoxide and the like, alkali metal amides such aslithium diisopropyl amide and the like and organic bases such astriethylamine, 1,4-diazabicyclo[2.2.2]octane,1,8-diazabicyclo[5.4.0]-7-undecene and the like.

The amount of base used for the reaction is usually 1 to 10 moles basedon 1 mole of the compound (r).

The amount of the compound (m) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (r).

The reaction temperature is usually in the range of −20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (I-10) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (I-10) may be purified, ifnecessary, by chromatography, recrystallization and the like.

(Production Method 11)

The production method by making react the compound (s) and the compound(o).

wherein R¹, R², R³⁻², R⁴ and X have the same meaning as described above.

The reaction is usually carried out in a solvent and in the presence ofa base.

The solvent used for the reaction includes, for example, acid amidessuch as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, water and the mixturethereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate and the like, alkali metal alkoxides such as sodium methoxide,potassium tert-butoxide and the like, alkali metal amides such aslithium diisopropyl amide and the like and organic bases such astriethylamine, 1,4-diazabicyclo[2.2.2]octane,1,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of base usedfor the reaction is usually 1 to 10 moles based on 1 mole of thecompound (o).

The amount of the compound (s) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (o).

The reaction temperature is usually in the range of −20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (I-10) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (I-10) may be purified, ifnecessary, by chromatography, recrystallization and the like.

(Production Method 12)

The compound (I-11) which n is 1 or 2 in the present compound can beproduced by making the compound (I-10) oxidize.

wherein R¹, R², R³⁻² and R⁴ have the same meaning as described above, n′represents 1 or 2.

The reaction is usually carried out in a solvent and in the presence ofa oxidizing agent.

The solvent used for the reaction includes, for example, alcohols suchas methanol, ethanol and the like, halogenated hydrocarbons such asdichloromethane, chloroform and the like, aromatic hydrocarbons such astoluene, xylene and the like, aliphatic carboxylic acids such as aceticacid, trifluoroacetic acid and the like, water and the mixture thereof.

The oxidizing agent used for the reaction includes, for example,peracids such as peracetic acid, trifluoroperacetic acid,m-chloroperbenzoic acid and the like, halogen molecules such as chlorineand bromine, halogenated succinimides such as N-chlorosuccinimide,perhalogenated compounds such as perchloric acid or its salts, periodicacid or its salts and the like, permanganates such as potassiumpermanganate and the like, chromic acid salts such as potassium chromateand the like and hydrogen peroxide. The amount of oxidizing agent usedfor the reaction is usually 1 to 10 moles based on 1 mole of thecompound (I-10).

The reaction temperature is usually in the range of −50 to 200° C. andthe reaction period is usually 1 to 72 hours.

After the reaction has finished, the compound (I-11) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (I-11) may be purified, ifnecessary, by chromatography, recrystallization and the like.

Next, the production method of intermediate compounds for production ofthe present compounds is explained as Reference Production Method.

(Reference Production Method 1-1)

The compound (g) can be produced by making the compound (I-6) hydrolyzein the presence of an acid.

wherein R¹, R³, R⁴ and n have the same meaning as described above, R⁵⁻³represents a methoxy group or an ethoxy group.

The reaction is usually carried out in the presence of water and usuallyin an organic solvent.

The organic solvent used for the reaction includes, for example,alcohols such as methanol, ethanol and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, aliphatic carboxylicacids such as formic acid, acetic acid and the like and the mixturethereof.

The acid used the reaction includes, for example, inorganic acids suchas hydrochloric acid, sulfuric acid and the like.

The amount of an acid used for the reaction is usually 1 to 10 molesbased on 1 mole of the compound (I-6).

The reaction temperature is usually in the range of −20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (g) can be isolated bysubjecting post-treatment such as pouring water to the reaction mixture,extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (g) may be purified, if necessary,by chromatography, recrystallization and the like.

(Reference Production Method 1-2)

The compound (g) can be produced by making the compound (I-6) hydrolyzein the presence of a base.

The reaction is usually carried out in the presence of water and usuallyin an organic solvent.

The organic solvent used for the reaction includes, for example,alcohols such as methanol, ethanol and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, aromatic hydrocarbons such astoluene, xylene and the like and the mixture thereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydroxide, potassium hydroxide and the like.

The amount of a base used for the reaction is usually 1 to 10 molesbased on 1 mole of the compound (I-6).

The reaction temperature is usually in the range of −20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (g) can be isolated bysubjecting post-treatment such as pouring water and an acid to thereaction mixture, extracting with an organic solvent, followed byconcentrating the organic layer. The isolated compound (g) may bepurified, if necessary, by chromatography, recrystallization and thelike.

(Reference Production Method 2)

The compound (d-1) which R³⁻² is a C1-C4 alkyl group in the compound (d)can be produced by making react the below compound (a) and the compound(k).

wherein R², R⁴, R³⁻¹, n and X have the same meaning as described above.

The reaction is usually carried out in a solvent and in the presence ofa base.

The solvent used for the reaction includes, for example, acid amidessuch as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, water and the mixturethereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate and the like, alkaline metal alkoxides such as sodiummethoxide, potassium tert-butoxide and the like, alkaline metal amidessuch as lithium diisopropylamide and the like and organic bases such astriethylamine, 1,4-diazabicyclo[2.2.2]octane,1,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of base usedfor the reaction is usually 1 to 10 moles based on 1 mole of thecompound (k).

The amount of the compound (a) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (k).

The reaction temperature is usually in the range of −20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (d-1) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (d-1) may be purified, itnecessary, by chromatography, recrystallization and the like.

(Reference Production Method 3)

The compound (k-1) which n is 0 and the compound (k-2) which n is 1 or 2can be produced, for example, according to following scheme.

wherein R², R⁴, X and n′ have the same meaning as described above.

(Step I-1-a)

The compound (k-1) can be produced by making react the compound (l) andthe compound (m).

The reaction is usually carried out in a solvent and in the presence ofa base.

The solvent used for the reaction includes, for example, acid amidessuch as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, water and the mixturethereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate and the like, alkaline metal alkoxides such as sodiummethoxide, potassium tert-butoxide and the like, alkaline metal amidessuch as lithium diisopropylamide and the like and organic bases such astriethylamine, 1,4-diazabicyclo[2.2.2]octane,1,8-diazabicyclo[5.4.0]-7-undecene and the like.

The amount of base used for the reaction is usually 1 to 10 moles basedon 1 mole of the compound (l).

The amount of the compound (m) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (l).

The reaction temperature is usually in the range of −20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (k-1) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (k-1) may be purified, ifnecessary, by chromatography, recrystallization and the like.

(Step III-1-b)

The compound (k-1) can also be produced by making react the compound (n)and the compound (o).

The reaction is usually carried out in a solvent and in the presence ofa base. The solvent used for the reaction includes, for example, acidamides such as N,N-dimethylformamide and the like, ethers such asdiethyl ether, tetrahydrofuran and the like, organic sulfurs such asdimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons suchas chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatichydrocarbons such as toluene, xylene and the like, water and the mixturethereof.

The base used for the reaction includes, for example, inorganic basessuch as sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate and the like, alkaline metal alkoxides such as sodiummethoxide, potassium tert-butoxide and the like, alkaline metal amidessuch as lithium diisopropylamide and the like and organic bases such astriethylamine, 1,4-diazabicyclo[2.2.2]octane,1,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of base usedfor the reaction is usually 1 to 10 moles based on 1 mole of thecompound (o).

The amount of the compound (n) used for the reaction is usually 1 to 10moles based on 1 mole of the compound (o).

The reaction temperature is usually in the range of 20 to 100° C. andthe reaction period is usually 1 to 24 hours.

After the reaction has finished, the compound (k-1) can be isolated bysubjecting post-treatment such as pouring the reaction mixture intowater, extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (k-1) may be purified, ifnecessary, by chromatography, recrystallization and the like.

(Step III-2)

The compound (k-2) can be produced, for examples by making the compound(k-1) oxidize.

The reaction is usually carried out in the presence of a solvent and inthe presence of a oxidizing agent.

The solvent used for the reaction includes, for example, alcohols suchas methanol, ethanol and the like, halogenated hydrocarbons such asdichloromethane, chloroform and the like, aromatic hydrocarbons such astoluene, xylene and the like, aliphatic carboxylic acids such as aceticacid, trifluoroacetic acid and the like, water and the mixture thereof.

The oxidizing agent used for the reaction includes, for example,peracids such as peracetic acid, trifluoroperacetic acid,m-chloroperbenzoic acid and the like, halogen molecules such as chlorineand bromine, halogenated succinimides such as N-chlorosuccinimide,perhalogenated compounds such as perchloric acid or its salts, periodicacid or its salts and the like, permanganates such as potassiumpermanganate and the like, chromic acid salts such as potassium chromateand the like and hydrogen peroxide. The amount of oxidizing agent usedfor the reaction is usually 1 to 10 moles based on 1 mole of thecompound (k-1).

The reaction temperature is usually in the range of −50 to 200° C. andthe reaction period is usually 1 to 72 hours.

After the reaction has finished, the compound (k-2) can be isolated bysubjecting a treatment such as pouring the reaction mixture into water,extracting with an organic solvent, followed by concentrating theorganic layer. The isolated compound (k-2) may be purified, ifnecessary, by chromatography, recrystallization and the like.

The above mentioned compound (o) and (s) each can be produced, forexample, by the same method described in The Journal of OrganicChemistry, 27(1), p. 93-95 (1962) and HETEROCYCLES, 24(5), p. 1331-1346(1986).

The above mentioned compound (t) can be produced, for example, by thesame method described in The Journal of Organic Chemistry, 18, p.1112-1116 (1953).

The noxious arthropods against which the present compound has controlactivity may include insect pests, acarine pests and the like. Specificexamples are listed below:

Hemiptera:

Delphacidae such as Laodelphax striatellus, Nilaparvata lugens,Sogatella furcifera and the like,

Deltocephalidae such as Nephotettix cincticeps, Nephotettix virescensand the like,

Aphididae such as Aphis gossypii, Myzus persicae, Brevicoryne brassicae,Macrosiphum euphorbiae, Aulacorthum solani, Rhopalosiphum padi,Toxoptera citricidus and the like,

Pentatomidae such as Nezara antennata, Riptortus clavetus, Eysarcorislewisi, Eysarcoris parvus, Plautia stali, Halyomorpha mista, Stenotusrubrovittatus, Trigonotylus ruficornis and the like,

Aleyrodidae such as Trialeurodes vaporariorum, Bemisia argentifolii andthe like,

Coccidae such as Aonidiella aurantii, Comstockaspis perniciosa, Unaspiscitri, Ceroplastes rubens, Icerya purchasi and the like,

Tingidae,

Cimicidae such as Cimex lectularius,

Psyllidae, and the like;

Lepidoptera:

Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, Notarchaderogata, Plodia interpunctella, Maruca testulalis, Hellula undalis,Pediasia teterrellus and the like,

Noctuidae such as Spodoptera litura, Pseudaletia separata, Thoricoplusiaspp., Heliothis spp., Helicoverpa spp. and the like,

Pieridae such as Pieris rapae and the like,

Tortricidae such as Adoxophyes spp., Grapholita molesta, Cydia pomonellaand the like,

Carposinidae such as Carposina niponensis and the like,

Lyonetiidae such as Lyonetia spp. and the like,

Lymantriidae such as tymantria spp., Euproctis spp., and the like,

Yponomeutidae such as Plutella xvlostella and the like,

Gracillariidae such as Caloptilia theivora, Phyllonorycter ringoneella,and the like,

Gelechiidae such as Pectinophora gossypiella and the like,

Arctiidae such as Hyphantria cunea and the like,

Tineidae such as Tinea translucens, Tineola bisselliella and the like;

Diptera:

Calicidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culexquinquefasciatus and the like,

Aedes spp. such as Aedes aegypti, Aedes albopictus and the like,

Anopheles spp. such as Anopheles sinensis and the like,

Chironomidae,

Muscidae such as Musca domestica, Muscina stabulans and the like,

Calliphoridae,

Sarcophagidae,

Fanniidae,

Anthomyiidae such as Delia platura, Delia antiqua and the like,

Agromyzidae such as Liriomyza trifolii,

Tephritidae,

Drosophilidae,

Phoridae such as Megaselia spiracularis,

Psychodidae such as Clogmia albipunctata,

Tabanidae,

Simuliidae,

Stomoxyidae, and the like;

Coleoptera:

Diabrotica spp. such as Diabrotica virgifera virgifera, Diabroticaundecimpunctata howardi and the like,

Scarabaeidae such as Anomala cuprea, Anomala rufocuprea and the like,

Curculionidae such as Sitophilus zeamais, Lissorhoptrus oryzophilus,Callosobruchuys chienensis and the like,

Tenebrionidae such as Tenebrio molitor, Tribolium castaneum and thelike,

Chrysomelidae such as Oulema oryzae, Aulacophora femoralis, Phyllotretastriolata, Leptinotarsa decemlineata and the like,

Dermestidae such as Dermestes maculates,

Anobiidae,

Epilachna spp. such as Epilachna vigintioctopunctata and the like,

Lyctidae,

Bostrychidae,

Cerambycidae,

Cerambycidae,

Paederus fuscipes and the like;

Blattodea: Blattella germanica, Periplaneta fuliginosa, Periplanetaamericana, Periplaneta brunnea, Blatta orientalis and the like;

Thysanoptera: Thrips palmi, Thrips tabaci, Frankliniella occidentalis,Frankliniella intonsa, Scirtothrips dorsalis and the like;

Hymenoptera:

Formicidae such as Monomorium pharaosis, Formica fusca japonica,Ochetellus glaber, Pristomyrmex pungens, Pheidole noda, Linepithemahumile and the like,

Vespidae,

bethylid wasp,

Tenthredinidae such as Athalia japonica, and the like;

Orthoptera: Gryllotalpidae, Acrididae, Gryllidae and the like;

Aphaniptera: Ctenocephalides felis, Ctenocephalides canis, Pulexirritans, Xenopsylla cheopis, and the like;

Anoplura: Pediculus humanus corporis, Phthirus pubis, Haematopinuseurysternus, Dalmalinia ovis, Haemaopinus suis and the like;

Isoptera: Reticulitermes speratus, Coptotermes formosanus,Rhinotermitidae such as Reticulitermes flavipes, Reticulitermeshesperus, Reticulitermes virginicus, Reticulitermes tibialis,Heterotermes aureus and the like, Kalotermitidae such as Incisitermesminor and the like; dampwood termites such as Zootermopsis nevadensisand the like;

Acarina:

Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai,Panonychus citri, Panonychus ulmi, Oligonychus spp., and the like,

Eriophyidae such as Aculops lycopers, Aculops pelekassi, Aculusschlechtendali, and the like,

Tarsonemidae such as Polyphagotarsonemus latus, and the like,

Tenuipalpidae,

Tuckerellidae,

Ixodidae such as Haemaphysalis longicornis, Haemaphysalis flava,Dermacentor variabilis, Haemaphysalis flava, Dermacentor taiwanicus,Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Boophilusmicroplus, Amblyomma americanum, Rhipicephalus sanguineus and the like,

Acaridae such as Tyrophagus putrescentiae, and the like,

Epidermoptidae such as Dermatophagoides farinae, Dermatophagoidesptrenyssnus, and the like,

Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Cheyletusmoorei, and the like,

Ornithonyssus bacoti, Ornithonyssus sylvairum, Dermanyssidae such asDermanyssus gallinae;

chiggers such as Leptotrombidium akamushi,

Araneae: Chiracanthium japonicum, Latrodectus hasseltii, and the like;

Chilopoda: Thereuonema hilgendorfi, Scolopendra subspinipes, and thelike;

Diplopoda: Oxidus gracilis, Nedyopus tambanus, and the like;

Isopoda: Armadillidium vulgare, and the like;

Gastropoda: Limax marginatus, Limax flavus, and the like.

The noxious arthropod controlling agent of the present inventioncomprises the present compound and a inert carrier. Usually the presentcompound is mixed with a solid carrier, a liquid carrier and/or agaseous carrier, and if necessary, added a surfactant and other adjuvantfor formulation to formulate to an emulsifiable concentrate, an oilsolution, a shampoo formulation, a flowable, a dust, a wettable powder,a granule, a paste formulation, a microcapsule, a foam, an aerosol, acarbon dioxide gas formulation, a tablet and a resin formulation. Theseformulations may be converted to use into a poison bait, a mosquitocoil, an electric mosquito mat, a smoking agent, a fumigant or sheet.

In the noxious arthropod controlling agent of the present invention, thepresent compound is usually contained in an amount of 0.1% to 95% byweight.

The solid carrier for formulation includes, for example, a fine powerand a granule of clays (e.g., kaolin clay, diatomite, bentonite,Fubasami clay, acid clay, etc.), synthetic hydrated silicon oxide, talc,ceramic, other inorganic minerals (e.g., sericite, quartz, sulfur,activated carbon, calcium carbonate, hydrated silica) or chemicalfertilizers (e.g., ammonium sulfate, ammonium phosphate, ammoniumnitrate, ammonium chloride, urea).

The liquid carrier for formulation includes, for example, aromatic oraliphatic hydrocarbons (e.g., xylene, toluene, alkylnaphthalene,phenylxylylethane, kerosine, light oil, hexane, cyclohexane),halogenated hydrocarbons (e.g., chlorobenzene, dichloromethane,dichloroethane, trichloroethane), alcohols (e.g., methanol, ethanol,isopropyl alcohol, butanol, hexanol, ethylene glycol), ethers (e.g.,diethyl ether, ethylene glycol dimethyl ether, diethylene glycolmonomethyl ether, diethylene glycol monoethyl ether, propylene glycolmonomethyl ether, tetrahydrofuran, dioxane), esters (e.g., ethylacetate, butyl acetate), ketones (e.g., acetone, methyl ethyl ketone,methyl isobutyl ketone, cyclohexanone), nitrites (e.g., acetonitrile,isobutyronitrile), sulfoxides (e.g., dimethylsulfoxide), acid amides(e.g., N,N-dimethylformamide, N,N-dimethylacetamide), vegetable oils(e.g., soy bean oil, cotton seed oil), vegetable essential oils (e.g.,orange oil, hyssop oil, lemon oil) and water.

The gaseous carrier for formulation includes, for example, butane gas,flon gas, liquefied petroleum gas (LPG), dimethyl ether, carbon dioxideand the like.

The surfactant includes, for example, alkyl sulfate salts, alkylsulfonicacid salts, alkylarylsulfonic acid salts, alkyl aryl ethers and theirpolyoxyethylene derivatives, polyethylene glycol ethers, polyhydricalcohol esters, and sugar alcohol derivatives.

The other adjuvant for formulation includes, binders, dispersants,stabilizers and the like, and specifically for example, casein, gelatin,polysaccharides (e.g., starch, gum arabic, cellulose derivatives,alginic acid), lignin derivatives, bentonite, sugars, syntheticwater-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone,polyacrylic acid), PAP (isopropyl acid phosphate), BHT(2,6-di-t-butyl-4-methylphenol), BHA (a mixture of2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), vegetableoils, mineral oils, fatty acids, and fatty acid esters.

The base for resin formulation includes, for example, polyvinyl chloridebased copolymer, polyurethane and the like. To these bases, ifnecessary, a plasticizer such as phthalates (e.g., dimethyl phthalate,dioctyl phthalate), adipates and stearic acid may be added. The resinformulation can be obtained by kneading the compound into the base usinga known kneader and then formulating by injection molding, extrusionmolding, press molding and the like, and further, if necessary, via aprocess for molding, cutting and the like, the resin formulation havinga specific form can be converted into a resin formulation such as board,film, tape, net, string and the like. These resin formulations can beconverted into, for example, an animal collar, an animal ear tag, asheet formulation, an attraction string, a gardening stick.

A base for the poison bait includes for example, grain powders,vegetable oils, sugars, and crystalline cellulose, and further, ifnecessary, antioxidants such as dibutylhydroxytoluene andnordihydroguaiaretic acid, preservatives such as dehydroacetic acid,agents for preventing children and pets from erroneously eating such ashot pepper powder, and pest-attractive flavors such as cheese flavor,onion flavor and peanut oil may be added to the base.

The noxious arthropod controlling agent of the present invention isused, for example, by applying to noxious•arthropods directly and/or ata habitat of noxious arthropods such as plant, animal soil and the like.

When the noxious arthropod controlling agent of the present invention isused for a control of pests in agriculture and forestry, the applicationamount is usually 1 to 10,000 g/ha, preferably 10 to 500 g/ha, as anactive ingredient. The emulsifiable concentrates, wettable powders,flowables, and microcapsule formulations are usually applied afterdilution with water to have an active ingredient concentration of 1 to1,000 ppm, while dusts and granules are usually applied as such. Theseformulations may be sprayed directly to the plant to be protected fromnoxious arthropods. The noxious arthropods living in the soil can becontrolled by treating the soil with these formulations, and theformulations can also be applied to treat seedbeds prior to the plantingplants or to treat planting holes or plant bottoms in the planting.Furthermore, the sheet formulation of the noxious arthropod controllingagent of the present invention can be applied by a method such aswinding around plants, stretching in the vicinity of plants and layingon the soil surface at the plant bottom.

When the noxious arthropod controlling agent of the present invention isused for a control of epidemic, the application amount is usually 0.001to 10 mg/m³ as an active ingredient in case of application for openspace, and 0.001 to 100 mg/m² as an active ingredient in case ofapplication for plane surface. The emulsifiable concentrates, wettablepowders and flowables are usually applied after dilution with water tohave an active ingredient concentration of 0.01 to 10,000 ppm, while oilsolutions, aerosols, smoking agents and poison baits are usually appliedas such.

When the noxious arthropod controlling agent of the present invention isused for a control of parasite living outside of a livestock such ascow, horse, pig, sheep, goat and chicken, and a small animal such asdog, cat, rat and mouse, the noxious arthropod controlling agent of thepresent invention can be applied to said animal by a veterinarily knownmethod. Specifically, for systemic control, the noxious arthropodcontrolling agent of the present invention is administered by means of,for example, a tablet, a mixture with feed, a suppository or aninjection (e.g., intramuscular, subcutaneous, intravenous,intraperitoneal), and for non-systemic control, it is applied by amethod such as spraying an oil solution or an aqueous liquidformulation, carrying out pour-on treatment or spot-on treatment,washing said animal with a shampoo formulation, attaching the resinformulation on said animal as a collar or an ear-tag, and the like. Whenit is administered to an animal, the amount of the present compound isusually in the range of 0.1 to 1,000 mg/kg body weight of the animal.

The noxious arthropod controlling agent of the present invention canalso be used in admixture or combination with other insecticides,nematocides, acaricides, fungicides, herbicides, plant growthregulators, synergists, fertilizers, soil conditioners, animal feeds,and the like.

The active ingredients of such other insecticide and acaricide include,for example, pyrethroid compounds such as allethrin, tetramethrin,prallethrin, phenothrin, resmethrin, cyphenothrin, permethrin,cypermethrin, alpha-cypermethrin, zeta-cypermethrin, deltamethrin,tralomethrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, flumethrin, imiprothrin, etofenprox, fenvalerate,esfenvalerate, fenpropathrin, silafluofen, bifenthrin, transfluthrin,flucythrinate, tau-fluvalinate, acrinathrin, tefluthrin, cycloprothrin,empenthrin, 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropancarboxylate,2,3,5,6-tetrafluoro-4-methoxymethylbenzyl3-(1-propenyl)-2,2-dimethylcyclopropancarboxylate and2,3,5,6-tetrafluoro-4-methylbenzyl3-(1-propenyl)-2,2-dimethylcyclopropancarboxylate; organophosphoruscompounds such as dichlorvos, fenitrothion, cyanophos, profenofos,sulprofos, phenthoate, isoxathion, tetrachlorvinphos, fenthion,chlorpyriphos, diazinon, acephate, terbufos, phorate, chlorethoxyfos,fosthiazate, ethoprophos, cadusafos and methidathion; carbamatecompounds such as propoxur, carbaryl, metoxadiazone, fenobucarb,methomyl, thiodicarb, alanycarb, benfuracarb, oxamyl, aldicarb andmethiocarb; benzoylphenylurea compounds such as lufenuron,chlorfluazuron, hexaflumuron, diflubenzuron, triflumuron, teflubenzuron,flufenoxuron, fluazuron, novaluron and triazuron; juvenile hormone-likesubstances such as pyriproxyfen, methoprene, hydroprene and fenoxycarb;neonicotinoid compounds such as acetamiprid, nitenpyram, thiacloprid,thiamethoxam, dinotefuran and clothianidin; N-phenylpyrazole compoundssuch as acetoprole and ethiprole; benzoylhydrazine compounds such astebufenozide, chromafenozide, methoxyfenozide and halofenozide;diafenthiuron; pymetrozine; flonicamid; triazamate; buprofezin;spinosad; emamectin benzoate; chlorfenapyr; indoxacarb; pyridalyl;cyromazine; fenpyroximate; tebufenpyrad; tolfenpyrad; pyridaben;pyrimidifen; fluacrypyrim; etoxazole; fenazaquin; acequinocyl;hexythiazox; clofentezine; fenbutatin oxide; dicofol, propargite;abamectin; milbemectin; amitraz; cartap; bensultap; thiocyclam;endosulfan; spirodiclofen; spiromesifen; Flubendiamide; andazadirachtin.

The other fungicide include, for example, strobilurin compounds such asazoxystrobin; organophosphorus compounds such as tolclofos-methyl; azolecompounds such as triflumizole, pefurazoate and difenoconazole;phthalide; flutolanil; validamycin; probenazole; diclomezine;pencycuron; dazomet; kasugamycin; IBP; pyroquilon; oxolinic acid;tricyclazole; ferimzone; mepronil; EDDP; isoprothiolane; carpropamid;diclocymet; furametpyr; fludioxonil; procymidone; and diethofencarb.

The present invention is constructed in more detail by productionexamples, formulation examples, test examples and the like.

Firstly, production examples of the present compound are illustrated.

Production Example 1

0.6 g of 1-iodo-3,3,3-trifluoropropane and 0.5 g of(3,3,3-trifluoropropylsulfonyl)acetonitrile were dissolved to 20 ml ofN,N-dimethylformamide. 0.1 g of sodium hydride (60% in oil) was addedthereto at room temperature, and the mixture the mixture was stirred for24 hours at the same temperature. Then 10% hydrochloric acid was addedto the reaction mixture and the mixture the mixture was extracted byethyl acetate. The organic layer was washed with saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate,then concentrated under reduced pressure. The obtained residue wassubjected to silica gel chromatography to obtain 1.44 g of5,5,5-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)pentanenitrile(referred as the present compound (1), hereinafter).

The Present Compound (1)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.00-4.07 (m, 1H), 3.44-3.62 (m, 2H),2.72-2.87 (m, 2H), 2.36-2.64 (m, 4H)

Production Example 2

0.7 g of 2,2,3,3,3-pentafluoropropyl trifluoromethansulfonate and 0.5 gof (3,3,3-trifluoropropylsulfonyl)acetonitrile were dissolved to 20 mlof N,N-dimethylformamide. 0.3 g of potassium carbonate was added theretoat room temperature, and the mixture the mixture was stirred for 40hours at the same temperature. Then 10% hydrochloric acid was added tothe reaction mixture and the mixture the mixture was extracted by ethylacetate. The organic layer was washed with saturated aqueous solution ofsodium chloride, dried over anhydrous magnesium sulfate, thenconcentrated under reduced pressure. The obtained residue was subjectedto silica gel chromatography to obtain 0.40 g of4,4,5,5,5-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)pentanenitrile(referred as the present compound (2), hereinafter).

The Present Compound (2)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.22 (dd, 1H), 3.54-3.72 (m, 2H), 2.76-3.06(m, 4H)

Production Example 3

0.6 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 0.4 g of(3,3,3-trifluoropropylsulfonyl)acetonitrile were dissolved to 20 ml ofN,N-dimethylformamide. 0.09 g of sodium hydride (60% in oil) was addedthereto at room temperature, and the mixture the mixture was stirred for20 hours at the same temperature. Then 10% hydrochloric acid was addedto the reaction mixture and the mixture the mixture was extracted byethyl acetate. The organic layer was washed with saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate,then concentrated under reduced pressure. The obtained residue wassubjected to silica gel chromatography to obtain 1.44 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (3), hereinafter).

The Present Compound (3)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.01-4.08 (m, 1H), 3.44-3.62 (m, 2H),2.73-2.88 (m, 2H), 2.28-2.62 (m, 4H)

Production Example 4

0.9 g of 2,2,3,3,4,4,4-heptafluorobutyl trifluoromethansulfonate and 0.5g of (3,3,3-trifluoropropylsulfonyl)acetonitrile were dissolved to 20 mlof N,N-dimethylformamide. 0.3 g of potassium carbonate was added theretoat room temperature, and the mixture the mixture was stirred for 28hours at the same temperature. Then 10% hydrochloric acid was added tothe reaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 0.40 g of4,4,5,5,6,6,6-heptafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (4), hereinafter).

The Present Compound (4)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.22 (dd, 1H), 3.55-3.72 (m, 2H), 2.78-3.10(m, 4H)

Production Example 5

0.8 g of 1-iodo-3,3,4,4,5,5,5-heptafluoropentane and 0.5 g of(3,3,3-trifluoropropylsulfonyl)acetonitrile were dissolved to 20 ml ofN,N-dimethylformamide. 0.1 g of sodium hydride (60% in oil) was addedthereto at room temperature, and the mixture was stirred for 24 hours atthe same temperature. Then 10% hydrochloric acid was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 0.45 g of5,5,6,6,7,7,7-heptafluoro-2-(3,3,3-trifluoropropylsulfonyl)heptanenitrile(referred as the present compound (5), hereinafter).

The Present Compound (5)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.04-4.08 (m, 1H), 3.46-3.63 (m, 2H),2.73-2.88 (m, 2H), 2.34-2.64 (m, 4H)

Production Example 6

1.3 g of 2,2,3,3,4,4,5,5-octafluoropentyl trifluoromethansulfonate and0.7 g of (3,3,3-trifluoropropylsulfonyl)acetonitrile were dissolved to30 ml of N,N-dimethylformamide. 0.5 g of potassium carbonate was addedthereto at room temperature, and the mixture was stirred for 20 hours atthe same temperature. Then 10% hydrochloric acid was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 0.32 g of4,4,5,5,6,6,7,7-octafluoro-2-(3,3,3-trifluoropropylsulfonyl)heptanenitrile(referred as the present compound (6), hereinafter).

The Present Compound (6)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.05 (tt, 1H), 4.21 (dd, 1H), 3.50-3.71 (m,2H), 2.70-3.09 (m, 4H)

Production Example 7

1.3 g of 1-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexane and 0.7 g of(3,3,3-trifluoropropylsulfonyl)acetonitrile were dissolved to 30 ml ofN,N-dimethylformamide. 0.1 g of potassium carbonate was added thereto atroom temperature, and the mixture was stirred for 6 hours at the sametemperature. Then 10% hydrochloric acid was added to the reactionmixture and the mixture was extracted by ethyl acetate. The organiclayer was washed with saturated aqueous solution of sodium chloride,dried over anhydrous magnesium sulfate, then concentrated under reducedpressure. The obtained residue was subjected to silica gelchromatography to obtain 0.59 g of5,5,6,6,7,7,8,8,8-nonafluoro-2-(3,3,3-trifluoropropylsulfonyl)octanenitrile(referred as the present compound (7), hereinafter).

The Present Compound (7)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.02-4.08 (m, 1H), 3.45-3.63 (m, 2H),2.73-2.86 (m, 2H), 2.34-2.63 (m, 4H)

Production Example 8

0.6 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 0.4 g of(3,3,4,4,4-pentafluorobutylsulfonyl)acetonitrile were dissolved to 50 mlof N,N-dimethylformamide. 0.5 g of sodium hydride (60% in oil) was addedthereto at room temperature, and the mixture was stirred for 4 days atthe same temperature. Then 10% hydrochloric acid was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 2.66 g of5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanenitrile(referred as the present compound (8), hereinafter).

The Present Compound (8)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.04-4.09 (m, 1H), 3.48-3.68 (m, 2H),2.67-2.82 (m, 2H), 2.31-2.61 (m, 4H)

Production Example 9

0.7 g of 2,2,3,3,4,4,4-heptafluorobutyl trifluoromethansulfonate and 0.5g of (3,3,4,4,4-pentafluorobutylsulfonyl)acetonitrile were dissolved to20 ml of N,N-dimethylformamide. 0.3 g of potassium carbonate was addedthereto at room temperature, and the mixture was stirred for 40 hours atthe same temperature. Then 10% hydrochloric acid was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 0.38 g of4,4,5,5,6,6,6-heptafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanenitrile(referred as the present compound (9), hereinafter).

The Present Compound (9)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.22 (dd, 1H), 3.56-3.76 (m, 2H), 2.68-3.10(m, 4H)

Production Example 10

1.8 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 2.0 g of(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)acetonitrile were dissolved to50 ml of N,N-dimethylformamide. 0.3 g of sodium hydride (60% in oil) wasadded thereto at room temperature, and the mixture was stirred for 20hours at the same temperature. Then 10% hydrochloric acid was added tothe reaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 1.43 g of2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-5,5,6,6,6-pentafluorohexanenitrile(referred as the present compound (10), hereinafter).

The Present Compound (10)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.07 (dd, 1H), 3.48-3.67 (m, 2H), 2.32-2.85(m, 6H)

Production Example 11

0.2 g of iodomethane and 0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrilewere dissolved to 20 ml of N,N-dimethylformamide. 0.06 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 20 hours at the same temperature. Then 10%hydrochloric acid was added to the reaction mixture and the mixture wasextracted by ethyl acetate. The organic layer was washed with saturatedaqueous solution of sodium chloride, dried over anhydrous magnesiumsulfate, then concentrated under reduced pressure. The obtained residuewas subjected to silica gel chromatography to obtain 0.35 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (11), hereinafter).

The Present Compound (11)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.40-3.58 (m, 2H), 2.73-2.88 (m, 2H),2.16-2.58 (m, 4H), 1.83 (s, 3H)

Production Example 12

0.3 g of iodomethane and 0.7 g of4,4,5,5,6,6,6-heptafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrilewere dissolved to 30 ml of N,N-dimethylformamide. 0.07 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 24 hours at the same temperature. Then 10%hydrochloric acid was added to the reaction mixture and the mixture wasextracted by ethyl acetate. The organic layer was washed with saturatedaqueous solution of sodium chloride, dried over anhydrous magnesiumsulfate, then concentrated under reduced pressure. The obtained residuewas subjected to silica gel chromatography to obtain 0.32 g of4,4,5,5,6,6,6-heptafluoro-2-methyl-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (12), hereinafter).

The Present Compound (12)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.48-3.65 (m, 2H), 2.61-3.13 (m, 4H), 2.00(d, 3H)

Production Example 13

0.2 g of iodomethane and 0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanenitrilewere dissolved to 20 ml of N,N-dimethylformamide. 0.05 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 20 hours at the same temperature. Then 10%hydrochloric acid was added to the reaction mixture and the mixture wasextracted by ethyl acetate. The organic layer was washed with saturatedaqueous solution of sodium chloride, dried over anhydrous magnesiumsulfate, then concentrated under reduced pressure. The obtained residuewas subjected to silica gel chromatography to obtain 0.49 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanenitrile(referred as the present compound (13), hereinafter).

The Present Compound (13)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.42-3.61 (m, 2H), 2.68-2.82 (m, 2H),2.18-2.58 (m, 4H), 1.84 (s, 3H)

Production Example 14

0.2 g of iodomethane and 0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)hexanenitrilewere dissolved to 20 ml of N,N-dimethylformamide. 0.05 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 2 days at the same temperature. Then 10%hydrochloric acid was added to the reaction mixture and the mixture wasextracted by ethyl acetate. The organic layer was washed with saturatedaqueous solution of sodium chloride, dried over anhydrous magnesiumsulfate, then concentrated under reduced pressure. The obtained residuewas subjected to silica gel chromatography to obtain 0.49 g of2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-2-methyl-5,5,6,6,6-pentafluorohexanenitrile(referred as the present compound (14), hereinafter).

The Present Compound (14)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.42-3.61 (m, 2H), 2.68-2.82 (m, 2H),2.18-2.58 (m, 4H), 1.84 (s, 3H)

Production Example 15

0.2 g of iodoethane and 0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrilewere dissolved to 20 ml of N,N-dimethylformamide. 0.06 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 10 hours at the same temperature. Then 10%hydrochloric acid was added to the reaction mixture and the mixture wasextracted by ethyl acetate. The organic layer was washed with saturatedaqueous solution of sodium chloride, dried over anhydrous magnesiumsulfate, then concentrated under reduced pressure. The obtained residuewas subjected to silica gel chromatography to obtain 0.37 g of2-ethyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (15), hereinafter).

The Present Compound (15)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.39-3.58 (m, 2H), 2.72-2.84 (m, 2H),2.32-2.56 (m, 4H), 2.06-2.26 (m, 2H), 1.28 (t, 3H)

Production Example 16

0.2 g of 1-iodopropane and 0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrilewere dissolved to 20 ml of N,N-dimethylformamide. 0.06 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 24 hours at the same temperature. Then 10%hydrochloric acid was added to the reaction mixture and the mixture wasextracted by ethyl acetate. The organic layer was washed with saturatedaqueous solution of sodium chloride, dried over anhydrous magnesiumsulfate, then concentrated under reduced pressure. The obtained residuewas subjected to silica gel chromatography to obtain 0.38 g of5,5,6,6,6-pentafluoro-2-propyl-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (16), hereinafter).

The Present Compound (16)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.38-3.58 (m, 2H), 2.72-2.86 (m, 2H),2.32-2.58 (m, 4H), 1.95-2.11 (m, 2H), 1.58-1.72 (m, 2H), 1.10 (t, 3H)

Production Example 17

0.2 g of 2-iodopropane and 0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrilewere dissolved to 20 ml of N,N-dimethylformamide. 0.06 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 6 hours at the same temperature, for 2 hours at60° C. and for 6 hours at 90° C. Then 10% hydrochloric acid was added tothe reaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 0.13 g of5,5,6,6,6-pentafluoro-2-(2-propyl)-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (17), hereinafter).

The Present Compound (17)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.39-3.60 (m, 2H), 2.70-2.87 (m, 2H),2.26-2.62 (m, 5H), 1.35 (d, 3H), 1.27 (d, 3H)

Production Example 18

0.3 g of 1-iodobutane and 0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrilewere dissolved to 20 ml of N,N-dimethylformamide. 0.06 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 8 hours at the same temperature. Then 10%hydrochloric acid was added to the reaction mixture and the mixture wasextracted by ethyl acetate. The organic layer was washed with saturatedaqueous solution of sodium chloride, dried over anhydrous magnesiumsulfate, then concentrated under reduced pressure. The obtained residuewas subjected to silica gel chromatography to obtain 0.28 g of2-butyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (18), hereinafter).

The Present Compound (18)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.38-3.58 (m, 2H), 2.72-2.86 (m, 2H),2.32-2.58 (m, 4H), 1.94-2.11 (m, 2H), 1.38-1.65 (m, 4H), 1.00 (t, 3H)

Production Example 19

0.3 g of 1-iodopentane and 0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrilewere dissolved to 20 ml of N,N-dimethylformamide. 0.06 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 20 hours at the same temperature. Then 10%hydrochloric acid was added to the reaction mixture and the mixture wasextracted by ethyl acetate. The organic layer was washed with saturatedaqueous solution of sodium chloride, dried over anhydrous magnesiumsulfate, then concentrated under reduced pressure. The obtained residuewas subjected to silica gel chromatography to obtain 0.28 g of2-(3,3,4,4,4-pentafluorobutyl)-2-(3,3,3-trifluoropropylsulfonyl)heptanenitrile(referred as the present compound (19), hereinafter).

The Present Compound (19)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.38-3.58 (m, 2H), 2.72-2.86 (m, 2H),2.32-2.58 (m, 4H), 1.94-2.11 (m, 2H), 1.38-1.65 (m, 6H), 1.00 (t, 3H)

Production Example 20

0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsuufonyl)hexanenitrile wasdissolved to 20 ml of tetrahydrofuran. 0.06 g of sodium hydride (60% inoil) was added thereto at 0° C., and the mixture was stirred for 0.5hours at the same temperature. Then 0.4 g of1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was addedto the mixture at the same temperature and the mixture was stirred for0.5 hours. Furthermore, the mixture was stirred at room temperature for10 hours. After that, 10% hydrochloric acid was added to the reactionmixture and the mixture was extracted by ethyl acetate. The organiclayer was washed with saturated aqueous solution of sodium chloride,dried over anhydrous magnesium sulfate, then concentrated under reducedpressure. The obtained residue was subjected to silica gelchromatography to obtain 0.37 g of2,5,5,6,6,6-hexafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (20), hereinafter).

The Present Compound (20)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.54-3.67 (m, 2H), 2.39-2.88 (m, 6H)

Production Example 21

0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsuufonyl)hexanenitrile wasdissolved to 20 ml of tetrahydrofuran. 0.06 g of sodium hydride (60% inoil) was added thereto at 0° C., and the mixture was stirred for 0.5hours at the same temperature. Then 0.2 g of N-chloro succinimide wasadded to the mixture at the same temperature and the mixture was stirredfor 0.5 hours. Furthermore, the mixture was stirred at room temperaturefor 3 days. After that, 10% hydrochloric acid was added to the reactionmixture and the mixture was extracted by ethyl acetate. The organiclayer was washed with saturated aqueous solution of sodium chloride,dried over anhydrous magnesium sulfate, then concentrated under reducedpressure. The obtained residue was subjected to silica gelchromatography to obtain 0.15 g of2-chloro-5,5,6,6,6-hentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (21), hereinafter).

The Present Compound (21)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.66-3.84 (m, 2H), 2.42-2.92 (m, 6H)

Production Example 22

2.0 g of 1-iodo-4,4,4-trifluorobutane and 2.0 g of methyl(3,3,3-trifluoropropylsulfonyl)acetate were dissolved to 20 ml ofN,N-dimethylformamide. 1.2 g of potassium carbonate was added thereto atroom temperature, and the mixture was stirred for 20 hours at the sametemperature. Then 10% hydrochloric acid was added to the reactionmixture and the mixture was extracted by ethyl acetate. The organiclayer was washed with saturated aqueous solution of sodium chloride,dried over anhydrous magnesium sulfate, then concentrated under reducedpressure. The obtained residue was subjected to silica gelchromatography to obtain 0.80 g of methyl6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl) hexanoate (referred asthe present compound (22), hereinafter).

The Present Compound (22)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.89 (s, 3H), 3.82-3.88 (m, 1H), 3.30-3.50(m, 2H), 2.62-2.77 (m, 2H), 2.10-2.24 (m, 4H), 1.64-1.75 (m, 2H)

Production Example 23

1.2 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 1.0 g of methyl(3,3,3-trifluoropropylsulfonyl)acetate were dissolved to 20 ml ofN,N-dimethylformamide. 0.6 g of potassium carbonate was added thereto atroom temperature, and it was stirred for 30 hours at the sametemperature. Then 10% hydrochloric acid was added to the reactionmixture and the mixture was extracted by ethyl acetate. The organiclayer was washed with saturated aqueous solution of sodium chloride,dried over anhydrous magnesium sulfate, then concentrated under reducedpressure. The obtained residue was subjected to silica gelchromatography to obtain 1.20 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (23), hereinafter).

The Present Compound (23)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.90 (s, 3H), 3.86-3.94 (m, 1H), 3.38-3.51(m, 2H), 2.63-2.78 (m, 2H), 2.38-2.53 (m, 2H), 2.18-2.34 (m, 2H)

Production Example 24

4.8 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 5.0 g of methyl(3,3,4,4,4-pentafluorobutylsulfonyl)acetate were dissolved to 50 ml ofN,N-dimethylformamide. 0.7 g of sodium hydride (60% in oil) was addedthereto at room temperature, and the mixture was stirred for 2 days atthe same temperature. Then 10% hydrochloric acid was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 4.69 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoate(referred as the present compound (24), hereinafter).

The Present Compound (24)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.91 (s, 3H), 3.89-3.97 (m, 1H), 3.44-3.51(m, 2H), 2.58-2.73 (m, 2H), 2.39-2.53 (m, 2H), 2.20-2.34 (m, 2H)

Production Example 25

0.5 g of 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 10 ml of dichloromethane. 2 drops ofN,N-dimethylformamide and 0.2 ml of oxalyl chloride were subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 2 hours at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 0.1 g of tert-butyl alcohol and 0.2 mlof triethylamine were added dropwise at room temperature. The mixturewas stirred at the same temperature for 1 hour. Saturated aqueoussolution of ammonium chloride was added to the reaction mixture and themixture was extracted by ethyl acetate. The organic layer was washedwith saturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The obtainedresidue was subjected to silica gel chromatography to obtain 0.42 g oftert-butyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (25), hereinafter).

The Present Compound (25)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.75-3.82 (m, 1H), 3.38-3.52 (m, 2H),2.63-2.78 (m, 2H), 2.18-2.46 (m, 4H), 1.53 (s, 9H)

Production Example 26

0.4 g of iodomethane and 1.0 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenoate weredissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodium hydride(60% in oil) was added thereto at room temperature, and the mixture wasstirred for 3 hours at the same temperature. Then 10% hydrochloric acidwas added to the reaction mixture and the mixture was extracted by ethylacetate. The organic layer was washed with saturated aqueous solution ofsodium chloride, dried over anhydrous magnesium sulfate, thenconcentrated under reduced pressure. The obtained residue was subjectedto silica gel chromatography to obtain 0.73 g of methyl2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (26), hereinafter).

The Present Compound (26)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.88 (s, 3H), 3.43-3.52 (m, 2H), 2.63-2.78(m, 2H), 2.08-2.54 (m, 4H), 1.70 (s, 3H)

Production Example 27

0.4 g of iodoethane and 1.0 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenoate weredissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodium hydride(60% in oil) was added thereto at room temperature, and the mixture wasstirred for 20 hours at the same temperature. Then 10% hydrochloric acidwas added to the reaction mixture and the mixture was extracted by ethylacetate. The organic layer was washed with saturated aqueous solution ofsodium chloride, dried over anhydrous magnesium sulfate, thenconcentrated under reduced pressure. The obtained residue was subjectedto silica gel chromatography to obtain 0.45 g of methyl2-ethyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (27), hereinafter).

The Present Compound (27)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.88 (s, 3H), 3.33-3.65 (m, 2H), 2.06-2.77(m, 8H), 1.04 (t, 3H)

Production Example 28

0.4 g of 1-iodopropane and 1.0 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenoate weredissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodium hydride(60% in oil) was added thereto at room temperature, and the mixture wasstirred for 20 hours at the same temperature. Then 10% hydrochloric acidwas added to the reaction mixture and the mixture was extracted by ethylacetate. The organic layer was washed with saturated aqueous solution ofsodium chloride, dried over anhydrous magnesium sulfate, thenconcentrated under reduced pressure. The obtained residue was subjectedto silica gel chromatography to obtain 0.89 g of methyl5,5,6,6,6-pentafluoro-2-propyl-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (28), hereinafter).

The Present Compound (28)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.87 (s, 3H), 3.32-3.66 (m, 2H), 1.96-2.76(m, 8H) 1.16-1.58 (m, 2H), 1.01 (t, 3H)

Production Example 29

0.05 g of sodium hydride (60% in oil) was added to a solution of 0.5 gof methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenoate in 20ml of tetrahydrofuran at 0° C. and the mixture was stirred for 0.5 hoursat the same temperature. Then 0.4 g of1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was addedthereto and the mixture was stirred for 0.5 hour. Furthermore, themixture was stirred at room temperature for 10 hours. 10% hydrochloricacid was added to the reaction mixture and the mixture was extracted byethyl acetate. The organic layer was washed with saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate,then concentrated under reduced pressure. The obtained residue wassubjected to silica gel chromatography to obtain 0.39 g of methyl2,5,5,6,6,6-hexafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (29), hereinafter).

The Present Compound (29)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.00 (s, 3H), 3.26-3.56 (m, 2H), 2.09-2.80(m, 6H)

Production Example 30

0.7 g of iodomethane and 2.0 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanenoatewere dissolved to 50 ml of N,N-dimethylformamide. 0.2 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 4 hours at the same temperature. Then 10%hydrochloric acid was added to the reaction mixture and the mixture wasextracted by ethyl acetate. The organic layer was washed with saturatedaqueous solution of sodium chloride, dried over anhydrous magnesiumsulfate, then concentrated under reduced pressure. The obtained residuewas subjected to silica gel chromatography to obtain 1.20 g of methyl2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoate(referred as the present compound (30), hereinafter).

The Present Compound (30)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.90 (s, 3H), 3.46-3.53 (m, 2H), 2.45-2.72(m, 3H), 2.09-2.34 (m, 3H), 1.71 (s, 3H)

Production Example 31

0.5 g of 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 10 ml of dichloromethane. 2 drops ofN,N-dimethylformamide and 0.2 ml of oxalyl chloride were subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 2 hours at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 0.2 g of ammonia (30% (w/w) aqueoussolution) was added dropwise thereto at room temperature. The mixturewas stirred at the same temperature for 2 hours. Saturated aqueoussolution of ammonium chloride was added to the reaction mixture and themixture was extracted by ethyl acetate. The organic layer was washedwith saturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The obtainedresidue was subjected to silica gel chromatography to obtain 0.24 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (31), hereinafter).

The Present Compound (31)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.34 (bs, 1H), 5.73 (bs, 1H), 3.73 (dd,1H), 3.21-3.42 (m, 2H), 2.64-2.73 (m, 2H), 2.12-2.48 (m, 4H)

Production Example 32

0.5 g of 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 10 ml of dichloromethane. 2 drops ofN,N-dimethylformamide and 0.2 ml of oxalyl chloride were subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 1 hour at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 0.3 g of methylamine (40% (w/w) aqueoussolution) was added dropwise thereto at room temperature. The mixturewas stirred at the same temperature for 2 hours. Saturated aqueoussolution of ammonium chloride was added to the reaction mixture and themixture was extracted by ethyl acetate. The organic layer was washedwith saturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The obtainedresidue was subjected to silica gel chromatography to obtain 0.26 g ofN-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (32), hereinafter).

The Present Compound (32)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.22 (bs, 1H), 3.63 (dd, 1H), 3.18-3.39 (m,2H), 2.94 (d, 3H), 2.60-2.73 (m, 2H), 2.08-2.50 (m, 4H)

Production Example 33

0.5 g of 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 10 ml of dichloromethane. 2 drops ofN,N-dimethylformamide and 0.2 ml of oxalyl chloride were subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 1 hour at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 0.5 g of dimethylamine (40% (w/w)aqueous solution) was added dropwise thereto at room temperature. Themixture was stirred at the same temperature for 2 hours. Saturatedaqueous solution of ammonium chloride was added to the reaction mixtureand the mixture was extracted by ethyl acetate. The organic layer waswashed with saturated aqueous solution of sodium chloride, dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theobtained residue was subjected to silica gel chromatography to obtain0.30 g ofN,N-dimethyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (33), hereinafter).

The Present Compound (33)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.31 (dd, 1H), 3.19-3.53 (m, 2H), 3.21 (s,3H), 3.09 (s, 3H), 2.57-2.70 (m, 2H), 1.98-2.54 (m, 4H)

Production Example 34

1.1 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 20 ml of dichloromethane. 2 drops ofN,N-dimethylformamide and 0.5 ml of oxalyl chloride was subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 2 hours at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 0.5 g of ammonia (30% (w/w) aqueoussolution) was added dropwise thereto at room temperature. The mixturewas stirred at the same temperature for 2 hours. Saturated aqueoussolution of ammonium chloride was added to the reaction mixture and themixture was extracted by ethyl acetate. The organic layer was washedwith saturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The obtainedresidue was subjected to silica gel chromatography to obtain 0.76 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (34), hereinafter).

The Present Compound (34)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.62 (bs, 1H), 5.74 (bs, 1H), 3.20-3.41 (m,2H), 2.64-2.78 (m, 2H), 2.08-2.54 (m, 4H), 1.68 (s, 3H)

Production Example 35

1.1 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 20 ml of dichloromethane. 2 drops ofN,N-dimethylformamide and 0.5 ml of oxalyl chloride was subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 2 hours at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 0.7 g of methylamine (30% (w/w) aqueoussolution) was added dropwise thereto at room temperature. The mixturewas stirred at the same temperature for 2 hours. Saturated aqueoussolution of ammonium chloride was added to the reaction mixture and themixture was extracted by ethyl acetate. The organic layer was washedwith saturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The obtainedresidue was subjected to silica gel chromatography to obtain 0.70 g ofN-methyl-2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (35), hereinafter).

The Present Compound (35)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.56 (bs, 1H), 3.14-3.39 (m, 2H), 2.91 (d,3H), 2.60-2.74 (m, 2H), 2.03-2.53 (m, 4H), 1.67 (s, 3H)

Production Example 36

0.5 g of 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 10 ml of dichloromethane. 2 drops ofN,N-dimethylformamide and 0.2 ml of oxalyl chloride was subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 1 hour at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 1.0 g of dimethylamine (40% (w/w)aqueous solution) was added dropwise thereto at room temperature. Themixture was stirred at the same temperature for 4 hours. Saturatedaqueous solution of ammonium chloride was added to the reaction mixtureand the mixture was extracted by ethyl acetate. The organic layer waswashed with saturated aqueous solution of sodium chloride, dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theobtained residue was subjected to silica gel chromatography to obtain0.97 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)-N,N-2-dimethyl-2-methylhexanamide(referred as the present compound (36), hereinafter).

The Present Compound (36)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.37 (dd, 2H), 3.16 (bs, 6H), 1.98-2.88 (m,6H), 1.82 (s, 3H)

Production Example 37

0.5 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 20 ml of dichloromethane. 1 drop ofN,N-dimethylformamide and 0.2 ml of oxalyl chloride were subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 2 hours at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 0.2 g of ethylamine (70% (w/w) aqueoussolution) was added dropwise thereto at room temperature. The mixturewas stirred at the same temperature for 8 hours. Saturated aqueoussolution of ammonium chloride was added to the reaction mixture and themixture was extracted by ethyl acetate. The organic layer was washedwith saturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The obtainedresidue was subjected to silica gel chromatography to obtain 0.41 g ofN-ethyl-2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (37), hereinafter).

The Present Compound (37)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.57 (bs, 1H), 3.13-3.44 (m, 4H), 2.61-2.74(m, 2H), 2.01-2.52 (m, 4H), 1.66 (s, 3H), 1.18 (t, 3H)

Production Example 38

0.5 g of2-ethyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 20 ml of dichloromethane. 1 drop ofN,N-dimethylformamide and 0.2 ml of oxalyl chloride was subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 2 hours at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 0.2 g of ammonia (30% (w/w) aqueoussolution) was added dropwise thereto at room temperature. The mixturewas stirred at the same temperature for 1 hour. Saturated aqueoussolution of ammonium chloride was added to the reaction mixture and themixture was extracted by ethyl acetate. The organic layer was washedwith saturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The obtainedresidue was subjected to silica gel chromatography to obtain 0.37 g of2-ethyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (38), hereinafter).

The Present Compound (38)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.59 (bs, 1H), 5.82 (bs, 1H), 3.19-3.48 (m,2H), 2.62-2.76 (m, 2H), 2.11-2.52 (m, 6H), 1.10 (t, 3H)

Production Example 39

0.6 g of 1-iodo-4,4,4-trifluorobutane and 0.5 g of(3,3,3-trifluoropropylsulfonyl)acetonitrile were dissolved to 20 ml ofN,N-dimethylformamide. 0.1 g of sodium hydride (60% in oil) was addedthereto at room temperature, and the mixture was stirred for 10 hours atthe same temperature. Then 10% hydrochloric acid was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 0.57 g of6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile (referredas the present compound (39), hereinafter).

The Present Compound (39)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.90-3.97 (m, 1H), 3.41-3.59 (m, 2H),2.68-2.88 (m, 2H), 1.78-2.36 (m, 6H)

Production Example 40

0.5 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 20 ml of dichloromethane. 2 drops ofN,N-dimethylformamide and 0.2 ml of oxalyl chloride were subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 2 hours at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 0.2 g of propylamine was added dropwiseto it. The mixture was stirred at the same temperature for 14 hours.Saturated aqueous solution of ammonium chloride was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate and concentrated underreduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 0.26 g of2-methyl-N-propyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (40), hereinafter).

The Present Compound (40)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.62 (bs, 1H), 3.11-3.38 (m, 4H), 2.00-2.74(m, 6H), 1.66 (s, 3H), 1.45-1.70 (m, 2H), 0.94 (t, 3H)

Production Example 41

0.5 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 20 ml of dichloromethane. 2 drops ofN,N-dimethylformamide and 0.2 ml of oxalyl chloride were subsequentlyadded dropwise thereto at room temperature, then the mixture was stirredfor 2 hours at the same temperature. Then the reaction mixture wasconcentrated under reduced pressure. The obtained residue was dissolvedto 20 ml of tetrahydrofuran and 0.2 g of isopropylamine was addeddropwise thereto at room temperature. The mixture was stirred at thesame temperature for 14 hours. Saturated aqueous solution of ammoniumchloride was added to the reaction mixture and the mixture was extractedby ethyl acetate. The organic layer was washed with saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The obtained residue was subjectedto silica gel chromatography to obtain 0.25 g ofN-isopropyl-2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (41), hereinafter).

The Present Compound (41)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.40 (bs, 1H), 4.05-4.18 (m, 1H), 3.10-3.39(m, 2H), 2.60-2.78 (m, 2H), 1.98-2.52 (m, 4H), 1.65 (s, 3H), 1.19 (dd,6H)

Production Example 42

0.9 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 1.1 g of methyl(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)acetate were dissolved to 20 mlof N,N-dimethylformamide. 0.1 g of sodium hydride (60% in oil) was addedthereto at room temperature, and the mixture was stirred for 3 days atthe same temperature. Then 10% hydrochloric acid was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 1.12 g of methyl2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-5,5,6,6,6-pentafluorohexanoate(referred as the present compound (42), hereinafter).

The Present Compound (42)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.91-3.95 (m, 1H), 3.91 (s, 3H), 3.41-3.53(m, 2H), 2.62-2.77 (m, 2H), 2.38-2.54 (m, 2H), 2.19-2.34 (m, 2H)

Production Example 43

0.2 g of iodomethane and 0.6 g of methyl2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-5,5,6,6,6-pentafluorohexanoatewere dissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodiumhydride (60% in oil) was added thereto at room temperature, and themixture was stirred for 10 hours at the same temperature. Then 10%hydrochloric acid was added to the reaction mixture and the mixture wasextracted by ethyl acetate. The organic layer was washed with saturatedaqueous solution of sodium chloride, dried over anhydrous magnesiumsulfate, then concentrated under reduced pressure. The obtained residuewas subjected to silica gel chromatography to obtain 0.41 g of methyl2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-2-methyl-5,5,6,6,6-pentafluorohexanoate(referred as the present compound (43), hereinafter).

The Present Compound (43)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.89 (s, 3H), 3.47-3.56 (m, 2H), 2.61-2.78(m, 2H), 1.95-2.56 (m, 4H), 1.71 (s, 3H)

Production Example 44

0.4 g of iodomethane and 1.0 g of methyl6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate weredissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodium hydride(60% in oil) was added thereto at room temperature, and the mixture wasstirred for 10 hours at the same temperature. Then 10% hydrochloric acidwas added to the reaction mixture and the mixture was extracted by ethylacetate. The organic layer was washed with saturated aqueous solution ofsodium chloride, dried over anhydrous magnesium sulfate, thenconcentrated under reduced pressure. The obtained residue was subjectedto silica gel chromatography to obtain 0.85 g of methyl2-methyl-6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (44), hereinafter).

The Present Compound (44)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.86 (s, 3H), 3.31-3.55 (m, 2H), 2.62-2.75(m, 2H), 1.95-2.33 (m, 4H), 1.67 (s, 3H), 1.43-1.80 (m, 2H)

Production Example 45

0.2 g of iodomethane and 0.5 g of6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile weredissolved to 20 ml of N,N-dimethylformamide. 0.06 g of sodium hydride(60% in oil) was added thereto at room temperature, and the mixture wasstirred for 10 hours at the same temperature. Then 10% hydrochloric acidwas added to the reaction mixture and the mixture was extracted by ethylacetate. The organic layer was washed with saturated aqueous solution ofsodium chloride, dried over anhydrous magnesium sulfate, thenconcentrated under reduced pressure. The obtained residue was subjectedto silica gel chromatography to obtain 0.37 g of2-methyl-6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile(referred as the present compound (45), hereinafter).

The Present Compound (45)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.40-3.55 (m, 2H), 2.73-2.88 (m, 2H),1.85-2.34 (m, 6H), 1.80 (s, 3H)

Production Example 46

1.0 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 1.0 g of ethyl2-(3,3,3-trifluoropropylsulfonyl)propionate were dissolved to 20 ml ofdimethylsulfoxide. 0.2 g of sodium hydride (60% in oil) was addedthereto at room temperature, and the mixture was stirred for 10 hours atthe same temperature, for 4 hours at 60° C. then for 4 hours at 90° C.After that, the reaction mixture was cooled to room temperature, then10% hydrochloric acid was added to the reaction mixture and the mixturewas extracted by ethyl acetate. The organic layer was washed withsaturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate, then concentrated under reduced pressure. Theobtained residue was subjected to silica gel chromatography to obtain0.47 g of ethyl2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (46), hereinafter).

The Present Compound (46)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.33 (q, 2H), 3.46-3.53 (m, 2H), 2.63-2.78(m, 2H), 2.08-2.54 (m, 4H), 1.69 (s, 3H), 1.34 (t, 3H)

Production Example 47

After dissolving 1.8 g of S-(3,3,3-trifluoropropyl)benzenethioate to 100ml of tetrahydrofuran, this solution was added with 1.5 ml of sodiummethoxide (28% (w/w) methanol solution) under ice cooling; and thenbeing added dropwise with 2.0 g of2-bromo-5,5,6,6,6-pentafluorohexanenitrile at the same temperature,followed by stirring at room temperature for 0.5 hours. The reactionmixture was added with 10% hydrochloric acid, followed by extractionwith ethyl acetate. The organic layer was subsequently washed with 10%hydrochloric acid and saturated aqueous solution of sodium chloride,dried over anhydrous magnesium sulfate, and then concentrated underreduced pressure. The obtained residue was subjected to a silica gelchromatography to obtain 1.6 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanenitrile(referred as the present compound (47), hereinafter).

The Present Compound (47)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.67 (t, 1H), 2.89-3.04 (m, 2H), 2.10-2.58(m, 6H)

Production Example 48

After dissolving 0.5 g of S-(3,3,3-trifluoropropyl)benzenethioate to 20ml of tetrahydrofuran, this solution was added with 0.4 ml of sodiummethoxide (28% (w/w) methanol solution) under ice cooling; and thenbeing added dropwise with 0.6 g of2-bromo-5,5,6,6,6-pentafluorohexanenitrile at the same temperature,followed by stirring at room temperature for 1 hour. The reactionmixture was added with 10% hydrochloric acid, followed by extractionwith ethyl acetate. The organic layer was subsequently washed with 10%hydrochloric acid and saturated aqueous solution of sodium chloride,dried over anhydrous magnesium sulfate, and then concentrated underreduced pressure. The obtained residue was dissolved to 20 ml ofchloroform, added with 0.5 g of peracetic acid (32% (w/w) acetic acidsolution) under ice cooling, and then stirred at the same temperaturefor 4 hours. The reaction mixture was raised to room temperature, andpoured into water, then the mixture was extracted by ethyl acetate. Theorganic layer was subsequently washed with saturated aqueous solution ofsodium hydrogencarbonate and saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 0.4 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfinyl)hexanenitrile(referred as the present compound (48), hereinafter).

The Present Compound (48)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.62-3.69 (m, 1H), 2.98-3.38 (m, 2H),2.25-2.82 (m, 6H)

Production Example 49

1.1 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid was dissolved to 20 ml of dichloromethane. This solution wassubsequently added dropwise with 2 drops of N,N-dimethylformamide and0.5 ml of oxalyl chloride at room temperature, and then stirred at thesame temperature for 2 hours. The reaction mixture was concentratedunder reduced pressure. The obtained residue was dissolved to 20 ml oftetrahydrofuran, followed by dropwise addition of 0.5 g of ammonia (30%(w/w) aqueous solution) at room temperature; and then being stirred atthe same temperature for 10 hours. The reaction mixture was added withsaturated aqueous solution of ammonium chloride, followed by extractionwith ethyl acetate. The organic layer was concentrated under reducedpressure. The obtained residue was added with the mixture of 1.2 g of2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide and20 ml of toluene, followed by heating under refluxing for 10 hours. Thereaction mixture was dropped to a room temperature, followed byconcentration under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 0.47 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanthioamide(referred as the present compound (49), hereinafter).

The Present Compound (49)

¹H-NMR (CDCl₃, TMS): δ (ppm) 8.03 (bs, 1H), 7.80 (bs, 1H), 3.19-3.44 (m,2H), 2.08-2.78 (m, 6H), 1.85 (s, 3H)

Production Example 50

After dissolving 0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanenitrile and 0.2g of iodomethane with 20 ml of tetrahydrofuran, this solution was addedwith 1.6 ml of sodium bis(trimethylsilyl)amide (1 M tetrahydrofuransolution) at −78° C. This mixture was stirred at the same temperaturefor 0.5 hours. The reaction mixture was added with 10% hydrochloricacid, followed by extraction with ethyl acetate. The organic layer wassubsequently washed with 10% hydrochloric acid and saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate, andthen concentrated under reduced pressure. The obtained residue wassubjected to a silica gel chromatography to obtain 0.4 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanenitrile(referred as the present compound (50), hereinafter).

The Present Compound (50)

¹H-NMR (CDCl₃, TMS): δ (ppm) 2.98 (t, 2H), 2.08-2.58 (m, 6H), 1.71 (s,3H)

Production Example 51

5.7 g of 1-iodo-3,3,4,4,5,5,5-heptafluoropentane and 5.0 g of methyl(3,3,4,4,4-pentafluorobutylsulfonyl)acetate were dissolved to 50 ml ofN,N-dimethylformamide. This solution was added with 0.7 g of sodiumhydride (60% in oil) at room temperature, followed by stirring at thesame temperature for 3 days. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 1.80 g of methyl5,5,6,6,7,7,7-heptafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptanoate(referred as the present compound (51), hereinafter).

The Present Compound (51)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.91 (s, 3H), 3.90-3.97 (m, 1H), 3.41-3.54(m, 2H), 2.20-2.73 (m, 6H)

Production Example 52

0.4 g of iodomethane and 1.3 g of methyl5,5,6,6,7,7,7-heptafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptanoatewere dissolved to 50 ml of N,N-dimethylformamide. This solution wasadded with 0.1 g of sodium hydride (60% in oil) at room temperature,followed by stirring at the same temperature for 3 hours. The reactionmixture was added with 10% hydrochloric acid, followed by extractionwith ethyl acetate. The organic layer was washed with saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate, andthen concentrated under reduced pressure. The obtained residue wassubjected to a silica gel chromatography to obtain 1.30 g of methyl5,5,6,6,7,7,7-heptafluoro-2-methyl-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptanoate(referred as the present compound (52), hereinafter).

The Present Compound (52)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.88 (s, 3H), 3.47-3.54 (m, 2H), 2.08-2.73(m, 6H), 1.71 (s, 3H)

Production Example 53

0.4 g of 1-iodo-3,3,3-trifluoropropane and 0.5 g of(3,3,4,4,4-pentafluorobutylsulfonyl)acetonitrile were dissolved to 20 mlof N,N-dimethylformamide. This solution was added with 0.08 g of sodiumhydride (60% in oil) at room temperature, followed by stirring at thesame temperature for 20 hours. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 0.26 g of2-(3,3,4,4,4-pentafluorobutylsulfonyl)-5,5,5-trifluoropentanenitrile(referred as the present compound (53), hereinafter).

The Present Compound (53)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.04-4.08 (m, 1H), 3.47-3.66 (m, 2H),2.35-2.81 (m, 6H)

Production Example 54

0.6 g of 1-iodo-3,3,4,4,5,5,5-heptafluoropentane and 0.5 g of(3,3,4,4,4-pentafluorobutylsulfonyl)acetonitrile were dissolved to 20 mlof N,N-dimethylformamide. This solution was added with 0.08 g of sodiumhydride (60% in oil) at room temperature, followed by stirring at thesame temperature for 24 hours. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 0.30 g of5,5,6,6,7,7,7-heptafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptanenitrile(referred as the present compound (54), hereinafter).

The Present Compound (54)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.16-4.22 (m, 1H), 3.50-3.68 (m, 2H),2.33-2.88 (m, 6H)

Production Example 55

0.5 g of5,5,6,6,7,7,7-heptafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptanoicacid was dissolved to 20 ml of dichloromethane. This solution wassubsequently added dropwise with 2 drops of N,N-dimethylformamide and0.1 ml of oxalyl chloride at room temperature, and then stirred at thesame temperature for 2 hours. The reaction mixture was concentratedunder reduced pressure. The obtained residue was dissolved to 20 ml oftetrahydrofuran, followed by dropwise addition of 0.2 g of ammonia (30%(w/w) aqueous solution) at room temperature; and then being stirred atthe same temperature for 2 hours. The reaction mixture was added withsaturated aqueous solution of ammonium chloride, followed by extractionwith ethyl acetate. The organic layer was concentrated under reducedpressure. The obtained residue was subjected to a silica gelchromatography to obtain 0.31 g of5,5,6,6,7,7,7-heptafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptaneamide(referred as the present compound (55), hereinafter).

The Present Compound (55)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.31 (bs, 1H), 5.73 (bs, 1H), 3.72-3.78 (m,1H), 3.24-3.45 (m, 2H), 2.12-2.74 (m, 6H

Production Example 56

1.1 g of5,5,6,6,7,7,7-heptafluoro-2-methyl-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptanoicacid was dissolved to 20 ml of dichloromethane. This solution wassubsequently added dropwise with 2 drops of N,N-dimethylformamide and0.4 ml of oxalyl chloride at room temperature, and then stirred at thesame temperature for 2 hours. The reaction mixture was concentratedunder reduced pressure. The obtained residue was dissolved to 50 ml oftetrahydrofuran, followed by dropwise addition of 0.4 g of ammonia (30%(w/w) aqueous solution) at room temperature; and then being stirred atthe same temperature for 2 hours. The reaction mixture was added withsaturated aqueous solution of ammonium chloride, followed by extractionwith ethyl acetate. The organic layer was concentrated under reducedpressure. The obtained residue was subjected to a silica gelchromatography to obtain 0.60 g of5,5,6,6,7,7,7-heptafluoro-2-methyl-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptaneamide(referred as the present compound (56), hereinafter).

The Present Compound (56)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.63 (bs, 1H), 5.76 (bs, 1H), 3.20-3.45 (m,2H), 2.08-2.73 (m, 6H), 1.70 (s, 3H)

Production Example 57

After dissolving 0.6 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanenitrilewith 30 ml of chloroform, this solution was added with 0.4 g ofperacetic acid (32% (w/w) acetic acid solution) under ice cooling,stirred at the same temperature for 2 hours, and then further stirred atroom temperature for 10 hours. The reaction mixture was poured intowater, followed by extraction with ethyl acetate. The organic layer wassubsequently washed with saturated aqueous solution of sodiumhydrogencarbonate and saturated aqueous solution of sodium chloride,dried over anhydrous magnesium sulfate, and then concentrated underreduced pressure. The obtained residue was subjected to a silica gelchromatography to obtain 0.25 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfinyl)hexanenitrile(referred as the present compound (57), hereinafter).

The Present Compound (57)

¹H-NMR (CDCl₃, TMS): δ (ppm) 2.98-3.21 (m, 2H), 2.60-2.82 (m, 2H),2.04-2.54 (m, 4H), 1.68 (s, 2H), 1.59 (s, 1H)

Production Example 58

0.8 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate wasdissolved to 50 ml of tetrahydrofuran. This solution was added with 0.08g of sodium hydride (60% in oil) at room temperature, followed bystirring at the same temperature for 0.5 hours; and then being addedwith 0.3 g of N-chlorosuccinimide at the same temperature, followed bystirring for 4 hours. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 0.60 g of methyl2-chloro-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (58), hereinafter).

The Present Compound (58)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.97 (s, 3H), 3.52-3.92 (m, 2H), 2.18-2.91(m, 6H)

Production Example 59

0.5 g of methyl2-chloro-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoatewas dissolved to 50 ml of methanol. This solution was added with 0.5 mlof ammonia (7 M methanol solution) at room temperature, followed bystirring at the same temperature for 2 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 0.15 g of2-chloro-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (59), hereinafter).

The Present Compound (59)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.88 (bs, 1H), 6.02 (bs, 1H), 3.38-3.74 (m,2H), 2.13-2.95 (m, 6H)

Production Example 60

0.5 g of5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoicacid was dissolved to 20 ml of dichloromethane. This solution wassubsequently added dropwise with 2 drops of N,N-dimethylformamide and0.2 ml of oxalyl chloride at room temperature, followed by stirring atthe same temperature for 4 hours. The reaction mixture was concentratedunder reduced pressure. The obtained residue was dissolved to 20 ml oftetrahydrofuran, followed by dropwise addition of 0.2 g of ammonia (30%(w/w) aqueous solution) at room temperature; and then being stirred atthe same temperature for 2 days. The reaction mixture was added withsaturated aqueous solution of ammonium chloride, followed by extractionwith ethyl acetate. The organic layer was concentrated under reducedpressure. The obtained residue was subjected to a silica gelchromatography to obtain 0.20 g of5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanamide(referred as the present compound (60), hereinafter).

The Present Compound (60)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.41 (bs, 1H), 5.73 (bs, 1H), 3.74-3.79 (m,1H), 3.20-3.45 (m, 2H), 2.08-2.74 (m, 6H)

Production Example 61

0.8 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoicacid was dissolved to 20 ml of dichloromethane. This solution wassubsequently added dropwise with 2 drops of N,N-dimethylformamide and0.3 ml of oxalyl chloride at room temperature, followed by stirring atthe same temperature for 4 hours. The reaction mixture was concentratedunder reduced pressure. The obtained residue was dissolved to 20 ml oftetrahydrofuran, followed by dropwise addition of 0.3 g of ammonia (30%(w/w) aqueous solution) at room temperature; and then being stirred atthe same temperature for 2 days. The reaction mixture was added withsaturated aqueous solution of ammonium chloride, followed by extractionwith ethyl acetate. The organic layer was concentrated under reducedpressure. The obtained residue was subjected to a silica gelchromatography to obtain 0.60 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanamide(referred as the present compound (61), hereinafter).

The Present Compound (61)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.69 (bs, 1H), 6.01 (bs, 1H), 3.22-3.46 (m,2H), 2.08-2.73 (m, 6H), 1.69 (s, 3H)

Production Example 62

After dissolving 2.0 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanenitrile with 50ml of methanol, this solution was added with 12.5 ml of sodium methoxide(28% (w/w) methanol solution) at room temperature, followed by stirringat the same temperature for 15 hours. This reaction mixture was addedwith 10% hydrochloric acid, followed by extraction with ethyl acetate.The organic layer was subsequently washed with 10% hydrochloric acid andsaturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate, and then concentrated under reduced pressure. Theobtained residue was subjected to a silica gel chromatography to obtain0.8 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanoate (referredas the present compound (62), hereinafter).

The Present Compound (62)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.79 (s, 3H), 3.31 (t, 1H), 2.72-2.90 (m,2H), 1.93-2.48 (m, 6H)

Production Example 63

After dissolving 0.3 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanoate with 20 mlof chloroform, this solution was added with 0.2 g of peracetic acid (32%(w/w) acetic acid solution) under ice cooling, followed by stirring atroom temperature for 6 hours. The reaction mixture was poured intowater, followed by extraction with ethyl acetate. The organic layer wassubsequently washed with saturated aqueous solution of sodiumhydrogencarbonate and saturated aqueous solution of sodium chloride,dried over anhydrous magnesium sulfate, and then concentrated underreduced pressure. The obtained residue was subjected to a silica gelchromatography to obtain 0.18 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfinyl)hexanoate(referred as the present compound (63), hereinafter).

The Present Compound (63)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.86 (s, 1.2H), 3.84 (s, 1.8H), 3.57-3.69(m, 1H), 2.13-3.14 (m, 8H)

Production Example 64

0.5 g of methyl2,5,5,6,6,6-hexafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate wasdissolved to 20 ml of methanol. This solution was added with 0.5 ml ofammonia (7 M methanol solution) at room temperature, followed bystirring at the same temperature for 0.5 hours; and then being furtheradded with 5 ml of ammonia (7 M methanol solution), followed by stirringat the same temperature for 2 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 0.37 g of2,5,5,6,6,6-hexafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (64), hereinafter).

The Present Compound (64)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.54 (bs, 1H), 5.88 (bs, 1H), 3.30-3.58 (m,2H), 2.14-2.83 (m, 6H)

Production Example 65

2.0 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate wasdissolved to 50 ml of tetrahydrofuran. This solution was added with 0.21g of sodium hydride (60% in oil) under ice cooling, followed by stirringat the same temperature for 0.5 hours; and then being added with 0.9 gof N-bromosuccinimide, followed by stirring at room temperature for 12hours. The reaction mixture was added with 10% hydrochloric acid,followed by extraction with ethyl acetate. The organic layer was washedwith saturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate, and then concentrated under reduced pressure. Theobtained residue was subjected to a silica gel chromatography to obtain0.30 g of methyl2-bromo-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (65), hereinafter).

The Present Compound (65)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.96 (s, 3H), 3.75-4.01 (m, 2H), 2.35-2.92(m, 6H)

Production Example 66

1.0 g of methyl2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-5,5,6,6,6-pentafluorohexanoatewas dissolved to 50 ml of tetrahydrofuran. This solution was added with0.08 g of sodium hydride (60% in oil) at 0° C., followed by stirring atthe same temperature for 0.5 hours; and subsequently being added with0.6 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate atthe same temperature, followed by stirring for 1 hour. The reactionmixture was added with 10% hydrochloric acid, followed by extractionwith ethyl acetate. The organic layer was washed with saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate, andthen concentrated under reduced pressure. The obtained residue wassubjected to a silica gel chromatography to obtain 0.75 g of methyl2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-2,5,5,6,6,6-hexafluorohexanoate(referred as the present compound (66), hereinafter).

The Present Compound (66)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.00 (s, 3H), 3.34-3.61 (m, 2H), 2.09-2.81(m, 6H)

Production Example 67

1.5 g of methyl2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-2,5,5,6,6,6-hexafluorohexanoatewas dissolved to 30 ml of methanol. This solution was added with 1.3 mlof ammonia (7 M methanol solution) at room temperature, followed bystirring at the same temperature for 24 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 1.10 g of2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-2,5,5,6,6,6-hexafluorohexanamide(referred as the present compound (67), hereinafter).

The Present Compound (67)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.54 (bs, 1H), 5.89 (bs, 1H), 3.34-3.62 (m,2H), 2.10-2.82 (m, 6H)

Production Example 68

After dissolving 0.3 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanoate and 0.12 gof iodomethane with 20 ml of tetrahydrofuran, this mixture was addedwith 0.9 ml of sodium bis(trimethylsilyl)amide (1 M tetrahydrofuransolution) at 0° C. The mixture was stirred at the same temperature for 1hour. The reaction mixture was added with 10% hydrochloric acid,followed by extraction with ethyl acetate. The organic layer wassubsequently washed with 10% hydrochloric acid and saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate, andthen concentrated under reduced pressure. The obtained residue wassubjected to a silica gel chromatography to obtain 0.3 g of methyl2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanoate(referred as the present compound (68), hereinafter).

The Present Compound (68)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.78 (s, 3H), 2.73-2.79 (m, 2H), 1.96-2.41(m, 6H), 1.50 (s, 3H)

Production Example 69

1.0 g of methyl2,5,5,6,6,6-hexafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate wasdissolved to 30 ml of methanol. This solution was added with 3.8 ml ofmethylamine (2 M methanol solution) at room temperature, followed bystirring at the same temperature for 2 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 0.92 g of2,5,5,6,6,6-hexafluoro-N-methyl-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (69), hereinafter).

The Present Compound (69)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.58 (bs, 1H), 3.26-3.58 (m, 2H), 2.99 (d,3H), 2.04-2.82 (m, 6H)

Production Example 70

After dissolving 1.0 g of methyl2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanoatewith 50 ml of methanol, this solution was added with an aqueous solutionof potassium hydroxide (a mixed solution of 0.9 g of potassium hydroxideand 5 ml of water) at room temperature, and then stirred at the sametemperature for 1 day. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was dissolved to 20 ml ofdichloromethane; and then being subsequently added dropwise with 2 dropsof N,N-dimethylformamide and 0.4 ml of oxalyl chloride at roomtemperature, and then stirred at the same temperature for 1 hour. Thereaction mixture was concentrated under reduced pressure. The obtainedresidue was dissolved to 20 ml of tetrahydrofuran, and then addeddropwise with 0.4 g of ammonia (30% (w/w) aqueous solution) at roomtemperature; and then being stirred at the same temperature for 1 hour.The reaction mixture was added with saturated aqueous solution ofammonium chloride, followed by extraction with ethyl acetate. Theorganic layer was concentrated under reduced pressure. The obtainedresidue was subjected to a silica gel chromatography to obtain 0.25 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanamide(referred as the present compound (70), hereinafter).

The Present Compound (70)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.60 (bs, 1H), 5.49 (bs, 1H), 2.73 (t, 2H),1.96-2.44 (m, 6H), 1.51 (s, 3H)

Production Example 71

After dissolving 4.4 g of methyl2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanoatewith 30 ml of chloroform, this solution was added with 2.9 g ofperacetic acid (32% (w/w) acetic acid solution) under ice cooling, andthen being stirred at the same temperature for 4 hours. The reactionmixture was poured into water, followed by extraction with ethylacetate. The organic layer was subsequently washed with saturatedaqueous solution of sodium hydrogencarbonate and saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate, andthen concentrated under reduced pressure. The obtained residue wassubjected to a silica gel chromatography to obtain 1.10 g of methyl2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfinyl)hexanoate(referred as the present compound (71), hereinafter).

The Present Compound (71)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.84 (s, 1.2H), 3.82 (s, 1.8H), 2.06-2.84(m, 8H), 1.53 (s, 1.2H), 1.52 (s, 1.8H)

Production Example 72

1.0 g of methyl2-(3,3,4,4,4-pentafluorobutylsulfonyl)-5,5,6,6,6-pentafluorohexanoatewas dissolved to 50 ml of tetrahydrofuran. This solution was added with0.09 g of sodium hydride (60% in oil) at room temperature, and thenstirred at the same temperature for 0.5 hours; and subsequently beingadded with 0.7 g of 1-fluoro-2,4,6-trimethylpyridiniumtrifluoromethanesulfonate at the same temperature, followed by stirringfor 3 hours. The reaction mixture was added with 10% hydrochloric acid,followed by extraction with ethyl acetate.

The organic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 0.78 g of methyl2,5,5,6,6,6-hexafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoate(referred as the present compound (72), hereinafter).

The Present Compound (72)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.00 (s, 3H), 3.33-3.60 (m, 2H), 2.08-2.81(m, 6H)

Production Example 73

0.6 g of methyl2,5,5,6,6,6-hexafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoatewas dissolved to 20 ml of methanol. This solution was added with 0.6 mlof ammonia (7 M methanol solution) at room temperature, and then stirredat the same temperature for 12 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 0.45 g of2,5,5,6,66-hexafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanamide(referred as the present compound (73), hereinafter).

The Present Compound (73)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.55 (bs, 1H), 5.91 (bs, 1H), 3.33-3.61 (m,2H), 2.04-2.83 (m, 6H)

Production Example 74

After dissolving 0.5 g of methyl2,5,5,6,6,6-hexafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate with30 ml of methanol, this solution was added with an aqueous solution ofpotassium hydroxide (a mixed solution of 0.4 g of potassium hydroxideand 5 ml of water) at room temperature, followed by stirring at the sametemperature for 12 hours. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The residue was dissolved to 20 ml ofdichloromethane; and then being subsequently added dropwise with 2 dropsof N,N-dimethylformamide and 0.2 ml of oxalyl chloride at roomtemperature, followed by stirring at the same temperature for 2 hours.The reaction mixture was concentrated under reduced pressure. Theobtained residue was dissolved to 30 ml of tetrahydrofuran, and thenadded dropwise with 0.4 g of dimethylamine (40% (w/w) aqueous solution)at room temperature; and then being stirred at the same temperature for2 hours. The reaction mixture was added with saturated aqueous solutionof ammonium chloride, followed by extraction with ethyl acetate. Theorganic layer was concentrated under reduced pressure. The obtainedresidue was subjected to a silica gel chromatography to obtain 0.26 g ofN,N-dimethyl-2,5,5,6,6,6-hexafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (74), hereinafter).

The Present Compound (74)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.32-3.55 (m, 2H), 3.29 (d, 3H), 3.10 (s,3H), 2.14-2.97 (m, 6H)

Production Example 75

1.0 g of methyl2-chloro-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoatewas dissolved to 30 ml of methanol. This solution was added with 3.6 mlof methylamine (2 M methanol solution) at room temperature, and thenstirred at the same temperature for 16 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 0.15 g of2-chloro-N-methyl-5,5,6,6,6-pentafluoro-2-(3,373-trifluoropropylsulfonyl)hexanamide(referred as the present compound (75), hereinafter).

The Present Compound (75)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.95 (bs, 1H), 3.35-3.75 (m, 2H), 2.96 (d,3H), 2.05-2.98 (m, 6H)

Production Example 76

1.0 g of 1-iodo-3,3,3-trifluoropropane and 1.0 g of methyl(3,3,3-trifluoropropylsulfonyl)acetate were dissolved to 20 ml ofdimethylsulfoxide. This solution was added with 0.6 g of potassiumcarbonate at room temperature, and then stirred at the same temperaturefor 16 hours. The reaction mixture was added with 10% hydrochloric acid,followed by extraction with ethyl acetate. The organic layer was washedwith saturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate, and then concentrated under reduced pressure. Theobtained residue was subjected to a silica gel chromatography to obtain0.42 g of methyl5,5,5-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)pentanoate (referred asthe present compound (76), hereinafter).

The Present Compound (76)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.90 (s, 3H), 3.88-3.94 (m, 1H), 3.36-3.52(m, 2H), 2.62-2.78 (m, 2H), 2.38-2.53 (m, 2H), 2.24-2.48 (m, 2H)

Production Example 77

1.0 g of methyl5,5,5-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)pentanoate wasdissolved to 30 ml of tetrahydrofuran. This solution was added with 0.12g of sodium hydride (60% in oil) at room temperature, followed bystirring at the same temperature for 0.5 hours; and then being addedwith 0.4 g of N-chlorosuccinimide at the same temperature, followed bystirring for 2 hours. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 0.65 g of methyl2-chloro-5,5,5-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)pentanate(referred as the present compound (77), hereinafter).

The Present Compound (77)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.97 (s, 3H), 3.58-3.88 (m, 2H), 2.35-2.88(m, 6H)

Production Example 78

2.0 g of methyl 1-iodo-4,4,4-trifluorobutane and 2.0 g of(3,3,3-trifluoropropylsulfonyl)acetate were dissolved to 30 ml ofdimethylsulfoxide. This solution was added with 1.2 g of potassiumcarbonate at room temperature, followed by stirring at the sametemperature for 3 days. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 1.50 g of methyl6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanate (referred asthe present compound (78), hereinafter).

The Present Compound (78)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.89 (s, 3H), 3.80-3.90 (m, 1H), 3.28-3.50(m, 2H), 2.60-2.78 (m, 2H), 2.09-2.27 (m, 4H), 1.62-1.75 (m, 2H)

Production Example 79

1.0 g of methyl6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate was dissolvedto 30 ml of tetrahydrofuran. This solution was added with 0.12 g ofsodium hydride (60% in oil) at room temperature, followed by stirring atthe same temperature for 0.5 hours; and then being added with 0.4 g ofN-chlorosuccinimide at the same temperature, followed by stirring for 4hours. The reaction mixture was added with 10% hydrochloric acid,followed by extraction with ethyl acetate. The organic layer was washedwith saturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate, and then concentrated under reduced pressure. Theobtained residue was subjected to a silica gel chromatography to obtain0.96 g of methyl2-chloro-6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate(referred as the present compound (79), hereinafter).

The Present Compound (79)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.96 (s, 3H), 3.53-3.84 (m, 2H), 2.12-2.79(m, 6H), 1.72-2.02 (m, 2H)

Production Example 80

0.8 g of methyl2-chloro-6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate wasdissolved to 20 ml of methanol. This solution was added with 0.9 ml ofammonia (7 M methanol solution) at room temperature, followed bystirring at the same temperature for 10 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 0.51 g of2-chloro-6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide(referred as the present compound (80), hereinafter).

The Present Compound (80)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.93 (bs, 1H), 6.20 (bs, 1H), 3.36-3.74 (m,2H), 2.13-2.81 (m, 6H), 1.61-2.01 (m, 2H)

Production Example 81

1.0 g of methyl2-chloro-5,5,5-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)pentanoate wasdissolved to 30 ml of methanol. This solution was added with 1.2 ml ofammonia (7 M methanol solution) at room temperature, followed bystirring at the same temperature for 14 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 0.62 g of2-chloro-5,5,5-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)pentanamide(referred as the present compound (81), hereinafter).

The Present Compound (81)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.93 (bs, 1H), 6.36 (bs, 1H), 3.38-3.73 (m,2H), 2.21-2.92 (m, 6H)

Production Example 32

2.8 g of 1-iodo-3,3,4,4,5,5,5-heptafluoropentane and 2.0 g of methyl(3,3,3-trifluoropropylsulfonyl)acetate were dissolved to 30 ml ofdimethylsulfoxide. This solution was added with 0.34 g of sodium hydride(60% in oil) at room temperature, and then stirred at the sametemperature for 14 hours. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 2.30 g of methyl5,5,6,6,7,7,7-heptafluoro-2-(3,3,3-trifluoropropylsulfonyl)heptanoate(referred as the present compound (82), hereinafter).

The Present Compound (82)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.91 (s, 3H), 3.87-3.95 (m, 1H), 3.36-3.52(m, 2H), 2.21-2.78 (m, 6H)

Production Example 83

1.0 g of methyl5,5,6,6,7,7,7-heptafluoro-2-(3,3,3-trifluoropropylsulfonyl)heptanoatewas dissolved to 30 ml of tetrahydrofuran. This solution was added with0.09 g of sodium hydride (60% in oil) at room temperature, and thenstirred at the same temperature for 0.5 hours; and then being added with0.3 g of N-chlorosuccinimide at the same temperature, followed bystirring for 1 hour, and then the reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 0.93 g of methyl2-chloro-5,5,6,6,7,7,7-heptafluoro-2-(3,3,3-trifluoropropylsulfonyl)heptanoate(referred as the present compound (83), hereinafter).

The Present Compound (83)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.97 (s, 3H), 3.53-3.90 (m, 2H), 2.30-2.91(m, 6H)

Production Example 84

0.7 g of methyl2-chloro-5,5,6,6,7,7,7-heptafluoro-2-(3,3,3-trifluoropropylsulfonyl)heptanoatewas dissolved to 30 ml of methanol. This solution was added with 0.6 mlof ammonia (7 M methanol solution) at room temperature, and then stirredat the same temperature for 10 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 0.50 g of2-chloro-5,5,6,6,7,7,7-heptafluoro-2-(3,3,3-trifluoropropylsulfonyl)heptanamide(referred as the present compound (84), hereinafter).

The Present Compound (84)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.88 (bs, 1H), 5.94 (bs, 1H), 3.37-3.73 (m,2H), 2.14-2.96 (m, 6H)

Production Example 85

7.0 g of 1-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexane and 4.4 g of methyl(3,3,3-trifluoropropylsulfonyl)acetate were dissolved to 50 ml ofdimethylsulfoxide. This solution was added with 2.59 g of potassiumcarbonate at room temperature. This mixture was stirred at 60° C. for 2days. The reaction mixture was dropped to about a room temperature. Thereaction mixture was added with 10% hydrochloric acid, followed byextraction with ethyl acetate. The organic layer was washed withsaturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate, and then concentrated under reduced pressure. Theobtained residue was subjected to a silica gel chromatography to obtain1.50 g of methyl5,5,6,6,7,7,8,8,8-nonafluoro-2-(3,3,3-trifluoropropylsulfonyl)octanoate(referred as the present compound (85), hereinafter).

The Present Compound (85)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.92 (s, 3H), 3.87-3.95 (m, 1H), 3.38-3.52(m, 2H), 2.20-2.78 (m, 6H)

Production Example 86

1.0 g of methyl5,5,6,6,7,7,8,8,8-nonafluoro-2-(3,3,3-trifluoropropylsulfonyl)octanoatewas dissolved to 30 ml of tetrahydrofuran. This solution was added with0.08 g of sodium hydride (60% in oil) at room temperature, followed bystirring at the same temperature for 0.5 hours; and then being addedwith 0.3 g of N-chlorosuccinimide at the same temperature, followed bystirring for 16 hours. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 0.89 g of methyl2-chloro-5,5,6,6,7,7,8,8,8-nonafluoro-2-(3,3,3-trifluoropropylsulfonyl)octanoate(referred as the present compound (86), hereinafter).

The Present Compound (86)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.97 (s, 3H), 3.58-3.92 (m, 2H), 2.33-2.94(m, 6H)

Production Example 87

0.8 g of methyl2-chloro-5,5,6,6,7,7,8,8,8-nonafluoro-2-(3,3,3-trifluoropropylsulfonyl)octanoatewas dissolved to 20 ml of methanol. This solution was added with 1.1 mlof ammonia (7 M methanol solution) at room temperature, followed bystirring at the same temperature for 12 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 0.45 g of2-chloro-5,5,6,6,7,7,8,8,8-nonafluoro-2-(3,3,3-trifluoropropylsulfonyl)octanamide(referred as the present compound (87), hereinafter).

The Present Compound (87)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.88 (bs, 1H), 5.93 (bs, 1H), 3.38-3.77 (m,2H), 2.15-2.98 (m, 6H)

Production Example 88

2.0 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoatewas dissolved to 30 ml of dimethylsulfoxide. This solution was addedwith 0.19 g of sodium hydride (60% in oil) at room temperature, followedby stirring at the same temperature for 0.5 hours; and then being addedwith 1.9 g of copper(II) chloride at the same temperature, followed bystirring for 12 hours. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure. The obtained residue was subjected to a silicagel chromatography to obtain 1.70 g of methyl2-chloro-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanate(referred as the present compound (88), hereinafter).

The Present Compound (88)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.98 (s, 3H), 3.63-3.93 (m, 2H), 2.29-2.92(m, 6H)

Production Example 89

1.5 g of methyl2-chloro-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoatewas dissolved to 30 ml of methanol. This solution was added with 1.4 mlof ammonia (7 M methanol solution) at room temperature, followed bystirring at the same temperature for 16 hours. The reaction mixture wasconcentrated under reduced pressure. The obtained residue was subjectedto a silica gel chromatography to obtain 1.10 g of2-chloro-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanamide(referred as the present compound (89), hereinafter).

The Present Compound (89)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.86 (bs, 1H), 5.93 (bs, 1H), 3.40-3.78 (m,2H), 2.13-2.95 (m, 6H)

The present compounds (90) to (103) shown below were produced by thesimilar method described above.

The Present Compound (90)

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.00 (s, 3H), 3.26-3.58 (m, 2H), 2.12-2.80(m, 6H)

The Present Compound (91)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.58 (bs, 1H), 5.92 (bs, 1H), 3.26-3.58 (m,2H), 2.19-2.83 (m, 6H)

The Present Compound (92)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.90 (s, 3H), 3.88-3.96 (m, 1H), 3.38-3.55(m, 2H), 2.54-2.73 (m, 2H), 2.23-2.50 (m, 4H)

The Present Compound (93)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.97 (s, 3H), 3.62-3.91 (m, 2H), 2.37-2.88(m, 6H)

The Present Compound (94)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.87 (bs, 1H), 6.01 (bs, 1H), 3.35-3.80 (m,2H), 2.19-2.92 (m, 6H)

The Present Compound (95)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.93-3.97 (m, 1H), 3.91 (s, 3H), 3.41-3.55(m, 2H), 2.21-2.73 (m, 6H)

The Present Compound (96)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.98 (s, 3H), 3.62-3.92 (m, 2H), 2.19-2.94(m, 6H)

The Present Compound (97)

¹H-NMR (CDCl₃ TMS): δ (ppm) 6.88 (bs, 1H), 5.95 (bs, 1H), 3.39-3.78 (m,2H), 2.14-2.96 (m, 6H)

The Present Compound (98)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.87 (s, 3H), 3.80-3.88 (m, 1H), 3.26-3.50(m, 2H), 2.59-2.78 (m, 2H), 2.03-2.18 (m, 4H), 1.44-1.72 (m, 4H)

The Present Compound (99)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.94 (s, 3H), 3.50-3.81 (m, 2H), 2.55-2.80(m, 3H), 2.05-2.32 (m, 3H), 1.50-1.80 (m, 4H)

The Present Compound (100)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.88 (bs, 1H), 5.98 (bs, 1H), 3.34-3.78 (m,2H), 2.58-2.81 (m, 3H), 2.01-2.28 (m, 3H), 1.40-1.82 (m, 4H)

The Present Compound (101)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.89 (s, 3H), 3.80-3.88 (m, 1H), 3.26-3.54(m, 2H), 2.59-2.80 (m, 3H), 2.00-2.26 (m, 3H), 1.65-1.78 (m, 2H)

The Present Compound (102)

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.96 (s, 3H), 3.50-3.85 (m, 2H), 2.61-2.78(m, 3H), 1.75-2.40 (m, 5H)

The Present Compound (103)

¹H-NMR (CDCl₃, TMS): δ (ppm) 6.95 (bs, 1H), 6.30 (bs, 1H), 3.35-3.78 (m,2H), 2.61-2.80 (m, 3H), 1.62-2.32 (m, 5H)

Next, examples of the present compound are described.

The compound given by the formula (I-A);

wherein R¹, R², R³ and R⁴ are the combination described in Table 1 toTable 83.

TABLE 1 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₃ CN H CF₃ CH₂CH₂CF₂CF₃ CN H CF₂CF₃CH₂CH₂CF₂CF₃ CN H CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CN CH₃ CF₃ CH₂CH₂CF₂CF₃ CN CH₃CF₂CF₃ CH₂CH₂CF₂CF₃ CN CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CN CH₂CH₃ CF₃CH₂CH₂CF₂CF₃ CN CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₃ CF₃ CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₃ CF₂CF₃CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CN CH(CH₃)₂ CF₃CH₂CH₂CF₂CF₃ CN CH(CH₃)₂ CF₂CF₃ CH₂CH₂CF₂CF₃ CN CH(CH₃)₂ CF₂CF₂CF₃CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₃ CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₂CF₃CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃CF₃ CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CNCH₂CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CN F CF₃ CH₂CH₂CF₂CF₃ CN F CF₂CF₃CH₂CH₂CF₂CF₃ CN F CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CN Cl CF₃ CH₂CH₂CF₂CF₃ CN ClCF₂CF₃ CH₂CH₂CF₂CF₃ CN Cl CF₂CF₂CF₃

TABLE 2 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₃ CO₂CH₃ H CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ HCF₂CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ CH₃ CF₃CH₂CH₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₂CF₃CH₂CH₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₃CH₂CH₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ F CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ F CF₂CF₃CH₂CH₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ Cl CF₃ CH₂CH₂CF₂CF₃CO₂CH₃ Cl CF₂CF₃ CH₂CH₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₃CO₂C(CH₃)₃ H CF₃ CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ H CF₂CF₃ CH₂CH₂CF₂CF₃CO₂C(CH₃)₃ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₃ CH₂CH₂CF₂CF₃CO₂C(CH₃)₃ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃CO₂C(CH₃)₃ F CF₃ CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ F CF₂CF₃ CH₂CH₂CF₂CF₃CO₂C(CH₃)₃ F CF₂CF₂CF₃

TABLE 3 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₃ CH₂CH₂CF₂CF₃CO₂C(CH₃)₃ Cl CF₂CF₃ CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₃CONH₂ H CF₃ CH₂CH₂CF₂CF₃ CONH₂ H CF₂CF₃ CH₂CH₂CF₂CF₃ CONH₂ H CF₂CF₂CF₃CH₂CH₂CF₂CF₃ CONH₂ CH₃ CF₃ CH₂CH₂CF₂CF₃ CONH₂ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃CONH₂ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CONH₂ CH₂CH₃ CF₃ CH₂CH₂CF₂CF₃ CONH₂CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CONH₂ FCF₃ CH₂CH₂CF₂CF₃ CONH₂ F CF₂CF₃ CH₂CH₂CF₂CF₃ CONH₂ F CF₂CF₂CF₃CH₂CH₂CF₂CF₃ CONH₂ Cl CF₃ CH₂CH₂CF₂CF₃ CONH₂ Cl CF₂CF₃ CH₂CH₂CF₂CF₃CONH₂ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₃) H CF₃ CH₂CH₂CF₂CF₃ CONH(CH₃) HCF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₃) H CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₃) CH₃ CF₃CH₂CH₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₃ CH₂CH₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃CH₂CH₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₂CF₃

TABLE 4 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₃ CONH(CH₃) F CF₃ CH₂CH₂CF₂CF₃ CONH(CH₃)F CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₃) ClCF₃ CH₂CH₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₂CF₃CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) H CF₃ CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) H CF₂CF₃CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) H CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₃CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₃ CH₂CH₂CF₂CF₃ CONH(CH₂CH₃)CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃CONH(CH₂CH₃) F CF₃ CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) F CF₂CF₃ CH₂CH₂CF₂CF₃CONH(CH₂CH₃) F CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) Cl CF₃ CH₂CH₂CF₂CF₃CONH(CH₂CH₃) Cl CF₂CF₃ CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) Cl CF₂CF₂CF₃CH₂CH₂CF₂CF₃ CON(CH₃)₂ H CF₃ CH₂CH₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₃CH₂CH₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₃CH₂CH₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₂CF₃

TABLE 5 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃ CH₂CH₂CF₂CF₃CON(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₃ CON(CH₃)₂ F CF₃ CH₂CH₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₃CH₂CH₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ CON(CH₃)₂ Cl CF₃CH₂CH₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₂CF₃CH₂CH₂CF₃ CN H CF₃ CH₂CH₂CF₃ CN H CF₂CF₃ CH₂CH₂CF₃ CN H CF₂CF₂CF₃CH₂CH₂CF₃ CN CH₃ CF₃ CH₂CH₂CF₃ CN CH₃ CF₂CF₃ CH₂CH₂CF₃ CN CH₃ CF₂CF₂CF₃CH₂CH₂CF₃ CN CH₂CH₃ CF₃ CH₂CH₂CF₃ CN CH₂CH₃ CF₂CF₃ CH₂CH₂CF₃ CN CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CF₃ CN F CF₃ CH₂CH₂CF₃ CN F CF₂CF₃ CH₂CH₂CF₃ CN FCF₂CF₂CF₃ CH₂CH₂CF₃ CN Cl CF₃ CH₂CH₂CF₃ CN Cl CF₂CF₃ CH₂CH₂CF₃ CN ClCF₂CF₂CF₃ CH₂CH₂CF₃ CO₂CH₃ H CF₃ CH₂CH₂CF₃ CO₂CH₃ H CF₂CF₃ CH₂CH₂CF₃CO₂CH₃ H CF₂CF₂CF₃

TABLE 6 R¹ R² R³ R⁴ CH₂CH₂CF₃ CO₂CH₃ CH₃ CF₃ CH₂CH₂CF₃ CO₂CH₃ CH₃ CF₂CF₃CH₂CH₂CF₃ CO₂CH₃ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₃ CO₂CH₃ F CF₃ CH₂CH₂CF₃ CO₂CH₃ FCF₂CF₃ CH₂CH₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CH₂CH₂CF₃ CO₂CH₃ Cl CF₃ CH₂CH₂CF₃CO₂CH₃ Cl CF₂CF₃ CH₂CH₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃ CH₂CH₂CF₃ CONH₂ H CF₃CH₂CH₂CF₃ CONH₂ H CF₂CF₃ CH₂CH₂CF₃ CONH₂ H CF₂CF₂CF₃ CH₂CH₂CF₃ CONH₂ CH₃CF₃ CH₂CH₂CF₃ CONH₂ CH₃ CF₂CF₃ CH₂CH₂CF₃ CONH₂ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₃CONH₂ CH₂CH₃ CF₃ CH₂CH₂CF₃ CONH₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₃ CONH₂ CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CF₃ CONH₂ F CF₃ CH₂CH₂CF₃ CONH₂ F CF₂CF₃ CH₂CH₂CF₃ CONH₂F CF₂CF₂CF₃ CH₂CH₂CF₃ CONH₂ Cl CF₃ CH₂CH₂CF₃ CONH₂ Cl CF₂CF₃ CH₂CH₂CF₃CONH₂ Cl CF₂CF₂CF₃ CH₂CH₂CF₃ CONH(CH₃) H CF₃ CH₂CH₂CF₃ CONH(CH₃) HCF₂CF₃ CH₂CH₂CF₃ CONH(CH₃) H CF₂CF₂CF₃

TABLE 7 R¹ R² R³ R⁴ CH₂CH₂CF₃ CONH(CH₃) CH₃ CF₃ CH₂CH₂CF₃ CONH(CH₃) CH₃CF₂CF₃ CH₂CH₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃ CH₂CH₂CF₃ CONH(CH₃) CH₂CH₃ CF₃CH₂CH₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CH₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₃ CONH(CH₃) F CF₃ CH₂CH₂CF₃ CONH(CH₃) F CF₂CF₃ CH₂CH₂CF₃CONH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CF₃ CONH(CH₃) Cl CF₃ CH₂CH₂CF₃ CONH(CH₃) ClCF₂CF₃ CH₂CH₂CF₃ CONH(CH₃) Cl CF₂CF₂CF₃ CH₂CH₂CF₃ CON(CH₃)₂ H CF₃CH₂CH₂CF₃ CON(CH₃)₂ H CF₂CF₃ CH₂CH₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃ CH₂CH₂CF₃CON(CH₃)₂ CH₃ CF₃ CH₂CH₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CF₃ CON(CH₃)₂ CH₃CF₂CF₂CF₃ CH₂CH₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃ CH₂CH₂CF₃ CON(CH₃)₂ CH₂CH₃CF₂CF₃ CH₂CH₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₃ CON(CH₃)₂ F CF₃CH₂CH₂CF₃ CON(CH₃)₂ F CF₂CF₃ CH₂CH₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃ CH₂CH₂CF₃CON(CH₃)₂ Cl CF₃ CH₂CH₂CF₃ CON(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CF₃ CON(CH₃)₂ ClCF₂CF₂CF₃

TABLE 8 R¹ R² R³ R⁴ CH₂CF₂CF₃ CN H CF₃ CH₂CF₂CF₃ CN H CF₂CF₃ CH₂CF₂CF₃CN H CF₂CF₂CF₃ CH₂CF₂CF₃ CN CH₃ CF₃ CH₂CF₂CF₃ CN CH₃ CF₂CF₃ CH₂CF₂CF₃ CNCH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ CN CH₂CH₃ CF₃ CH₂CF₂CF₃ CN CH₂CH₃ CF₂CF₃CH₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ CN F CF₃ CH₂CF₂CF₃ CN F CF₂CF₃CH₂CF₂CF₃ CN F CF₂CF₂CF₃ CH₂CF₂CF₃ CN Cl CF₃ CH₂CF₂CF₃ CN Cl CF₂CF₃CH₂CF₂CF₃ CN Cl CF₂CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ H CF₃ CH₂CF₂CF₃ CO₂CH₃ HCF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ CH₃ CF₃ CH₂CF₂CF₃CO₂CH₃ CH₃ CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ F CF₃CH₂CF₂CF₃ CO₂CH₃ F CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃Cl CF₃ CH₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃

TABLE 9 R¹ R² R³ R⁴ CH₂CF₂CF₃ CN H CF₃ CH₂CF₂CF₃ CN H CF₂CF₃ CH₂CF₂CF₃CN H CF₂CF₂CF₃ CH₂CF₂CF₃ CN CH₃ CF₃ CH₂CF₂CF₃ CN CH₃ CF₂CF₃ CH₂CF₂CF₃ CNCH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ CN CH₂CH₃ CF₃ CH₂CF₂CF₃ CN CH₂CH₃ CF₂CF₃CH₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ CN F CF₃ CH₂CF₂CF₃ CN F CF₂CF₃CH₂CF₂CF₃ CN F CF₂CF₂CF₃ CH₂CF₂CF₃ CN Cl CF₃ CH₂CF₂CF₃ CN Cl CF₂CF₃CH₂CF₂CF₃ CN Cl CF₂CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ H CF₃ CH₂CF₂CF₃ CO₂CH₃ HCF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ CH₃ CF₃ CH₂CF₂CF₃CO₂CH₃ CH₃ CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ F CF₃CH₂CF₂CF₃ CO₂CH₃ F CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃Cl CF₃ CH₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃ CH₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃

TABLE 10 R¹ R² R³ R⁴ CH₂CF₂CF₃ CONH₂ H CF₃ CH₂CF₂CF₃ CONH₂ H CF₂CF₃CH₂CF₂CF₃ CONH₂ H CF₂CF₂CF₃ CH₂CF₂CF₃ CONH₂ CH₃ CF₃ CH₂CF₂CF₃ CONH₂ CH₃CF₂CF₃ CH₂CF₂CF₃ CONH₂ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ CONH₂ CH₂CH₃ CF₃CH₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₃ CH₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃CONH₂ F CF₃ CH₂CF₂CF₃ CONH₂ F CF₂CF₃ CH₂CF₂CF₃ CONH₂ F CF₂CF₂CF₃CH₂CF₂CF₃ CONH₂ Cl CF₃ CH₂CF₂CF₃ CONH₂ Cl CF₂CF₃ CH₂CF₂CF₃ CONH₂ ClCF₂CF₂CF₃ CH₂CF₂CF₃ CONH(CH₃) H CF₃ CH₂CF₂CF₃ CONH(CH₃) H CF₂CF₃CH₂CF₂CF₃ CONH(CH₃) H CF₂CF₂CF₃ CH₂CF₂CF₃ CONH(CH₃) CH₃ CF₃ CH₂CF₂CF₃CONH(CH₃) CH₃ CF₂CF₃ CH₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃CONH(CH₃) CH₂CH₃ CF₃ CH₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CF₂CF₃CONH(CH₃) CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ CONH(CH₃) F CF₃ CH₂CF₂CF₃ CONH(CH₃)F CF₂CF₃ CH₂CF₂CF₃ CONH(CH₃) F CF₂CF₂CF₃

TABLE 11 R¹ R² R³ R⁴ CH₂CF₂CF₃ CONH(CH₃) Cl CF₃ CH₂CF₂CF₃ CONH(CH₃) ClCF₂CF₃ CH₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₂CF₃ CH₂CF₂CF₃ CON(CH₃)₂ H CF₃CH₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₃ CH₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃ CH₂CF₂CF₃CON(CH₃)₂ CH₃ CF₃ CH₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CH₂CF₂CF₃ CON(CH₃)₂ CH₃CF₂CF₂CF₃ CH₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃ CH₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃CF₂CF₃ CH₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ CON(CH₃)₂ F CF₃CH₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₃ CH₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃ CH₂CF₂CF₃CON(CH₃)₂ Cl CF₃ CH₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₃ CH₂CF₂CF₃ CON(CH₃)₂ ClCF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CN H CF₃ CH₂CF₂CF₂CF₃ CN H CF₂CF₃ CH₂CF₂CF₂CF₃ CNH CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CN CH₃ CF₃ CH₂CF₂CF₂CF₃ CN CH₃ CF₂CF₃CH₂CF₂CF₂CF₃ CN CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CN CH₂CH₃ CF₃ CH₂CF₂CF₂CF₃ CNCH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃

TABLE 12 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₃ CN F CF₃ CH₂CF₂CF₂CF₃ CN F CF₂CF₃CH₂CF₂CF₂CF₃ CN F CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CN Cl CF₃ CH₂CF₂CF₂CF₃ CN ClCF₂CF₃ CH₂CF₂CF₂CF₃ CN Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₃CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃CH₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃CO₂CH₃ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ F CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ FCF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₃CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃CH₂CF₂CF₂CF₃ CN H CF₃ CH₂CF₂CF₂CF₃ CN H CF₂CF₃ CH₂CF₂CF₂CF₃ CN HCF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CN CH₃ CF₃ CH₂CF₂CF₂CF₃ CN CH₃ CF₂CF₃CH₂CF₂CF₂CF₃ CN CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CN CH₂CH₃ CF₃ CH₂CF₂CF₂CF₃ CNCH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃

TABLE 13 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₃ CN F CF₃ CH₂CF₂CF₂CF₃ CN F CF₂CF₃CH₂CF₂CF₂CF₃ CN F CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CN Cl CF₃ CH₂CF₂CF₂CF₃ CN ClCF₂CF₃ CH₂CF₂CF₂CF₃ CN Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₃CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃CH₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃CO₂CH₃ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ F CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ FCF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₃CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃ CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃CH₂CF₂CF₂CF₃ CONH₂ H CF₃ CH₂CF₂CF₂CF₃ CONH₂ H CF₂CF₃ CH₂CF₂CF₂CF₃ CONH₂H CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CONH₂ CH₃ CF₃ CH₂CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₃CH₂CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₃CH₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₂CF₃

TABLE 14 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₃ CONH₂ F CF₃ CH₂CF₂CF₂CF₃ CONH₂ FCF₂CF₃ CH₂CF₂CF₂CF₃ CONH₂ F CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CONH₂ Cl CF₃CH₂CF₂CF₂CF₃ CONH₂ Cl CF₂CF₃ CH₂CF₂CF₂CF₃ CONH₂ Cl CF₂CF₂CF₃CH₂CF₂CF₂CF₃ CONH(CH₃) H CF₃ CH₂CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₃CH₂CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₃CH₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃CH₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₃ CH₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃CH₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CONH(CH₃) F CF₃CH₂CF₂CF₂CF₃ CONH(CH₃) F CF₂CF₃ CH₂CF₂CF₂CF₃ CONH(CH₃) F CF₂CF₂CF₃CH₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₃ CH₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₃CH₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₃CH₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₃ CH₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃CH₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₃ CH₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃CH₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₂CF₃

TABLE 15 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃ CH₂CF₂CF₂CF₃CON(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃CH₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₃ CH₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₃CH₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₃CH₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₃ CH₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CN H CF₃ CH₂CH₂CF₂CF₂CF₃ CN H CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CNH CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CN CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃ CN CH₃ CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CN CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CN CH₂CH₃ CF₃CH₂CH₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CN F CF₃ CH₂CH₂CF₂CF₂CF₃ CN F CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CNF CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CN Cl CF₃ CH₂CH₂CF₂CF₂CF₃ CN Cl CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CN Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₃CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃

TABLE 16 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃CO₂CH₃ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃CO₂CH₃ F CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ FCF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CN H CF₃CH₂CH₂CF₂CF₂CF₃ CN H CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CN H CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CN CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃ CN CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃CN CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CN CH₂CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃ CN CH₂CH₃CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CN F CF₃CH₂CH₂CF₂CF₂CF₃ CN F CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CN F CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CN Cl CF₃ CH₂CH₂CF₂CF₂CF₃ CN Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₃CN Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ HCF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃

TABLE 17 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃CO₂CH₃ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃CO₂CH₃ F CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ FCF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₃ CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH₂ H CF₃CH₂CH₂CF₂CF₂CF₃ CONH₂ H CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH₂ H CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CONH₂ CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₃CH₂CH₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH₂ CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH₂ F CF₃ CH₂CH₂CF₂CF₂CF₃ CONH₂ F CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CONH₂ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH₂ Cl CF₃CH₂CH₂CF₂CF₂CF₃ CONH₂ Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH₂ Cl CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) H CF₃ CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₂CF₃

TABLE 18 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃CONH(CH₃) CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃CONH(CH₃) F CF₃ CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) F CF₂CF₃ CH₂CH₂CF₂CF₂CF₃CONH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) F CF₃ CH₂CH₂CF₂CF₂CF₃CONH(CH₃) F CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃CONH(CH₃) Cl CF₃ CH₂CH₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₃CONH(CH₃) Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₃ CH₂CH₂CF₂CF₂CF₃CON(CH₃)₂ H CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃CON(CH₃)₂ CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃CON(CH₃)₂ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₃ CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ FCF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃

TABLE 19 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₃ CH₂CH₂CF₂CF₂CF₃CON(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CN H CF₃ CH₂CF₂CF₂CF₂CF₂H CN H CF₂CF₃ CH₂CF₂CF₂CF₂CF₂HCN H CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CN CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H CN CH₃CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CN CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CN CH₂CH₃ CF₃CH₂CF₂CF₂CF₂CF₂H CN CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CN CH₂CH₃ CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CN F CF₃ CH₂CF₂CF₂CF₂CF₂H CN F CF₂CF₃ CH₂CF₂CF₂CF₂CF₂HCN F CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CN Cl CF₃ CH₂CF₂CF₂CF₂CF₂H CN Cl CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CN Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ H CF₃CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ H CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ H CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ CH₃ CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ F CF₃CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ F CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ F CF₂CF₂CF₃

TABLE 20 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ Cl CF₃ CH₂CF₂CF₂CF₂CF₂HCO₂CH₃ Cl CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂HCN H CF₃ CH₂CF₂CF₂CF₂CF₂H CN H CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CN H CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CN CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H CN CH₃ CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CN CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CN CH₂CH₃ CF₃CH₂CF₂CF₂CF₂CF₂H CN CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CN CH₂CH₃ CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CN F CF₃ CH₂CF₂CF₂CF₂CF₂H CN F CF₂CF₃ CH₂CF₂CF₂CF₂CF₂HCN F CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CN Cl CF₃ CH₂CF₂CF₂CF₂CF₂H CN Cl CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CN Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ H CF₃CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ H CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ H CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ CH₃ CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ F CF₃CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ F CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ F CF₂CF₂CF₃

TABLE 21 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ Cl CF₃ CH₂CF₂CF₂CF₂CF₂HCO₂CH₃ Cl CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CO₂CH₃ Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂HCONH₂ H CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ H CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ HCF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ CH₃CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂CH₂CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ F CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ FCF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ F CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ Cl CF₃CH₂CF₂CF₂CF₂CF₂H CONH₂ Cl CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH₂ Cl CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) H CF₃ CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) H CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) H CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) CH₃CF₃ CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) CH₃CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) CH₂CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂HCONH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) CH₂CH₃ CF₂CF₂CF₃

TABLE 22 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) F CF₃ CH₂CF₂CF₂CF₂CF₂HCONH(CH₃) F CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) F CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) Cl CF₃ CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) Cl CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CONH(CH₃) Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ H CF₃CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ H CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ HCF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂HCON(CH₃)₂ CH₂CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ CH₂CH₃ CF₂CF₃CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ FCF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ F CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ FCF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ Cl CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂Cl CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H CON(CH₃)₂ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CNH CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN H CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN H CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CN CH₃ CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN CH₃ CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CN CH₃ CF₂CF₂CF₃

TABLE 23 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₃ CH₂CH₂CF₂CF₂CF₂CF₃CN CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CN F CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN F CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CN F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN Cl CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CN Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN Cl CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ FCF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃Cl CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ ClCF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN H CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN H CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CN H CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN CH₃ CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CN CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN CH₃ CF₂CF₂CF₃

TABLE 24 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₃ CH₂CH₂CF₂CF₂CF₂CF₃CN CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CN F CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN F CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CN F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN Cl CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CN Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CN Cl CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ FCF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃Cl CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CO₂CH₃ ClCF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ H CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ HCF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ CH₃CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ CH₃CF₂CF₂CF₃

TABLE 25 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ F CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ FCF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ ClCF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH₂ ClCF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) H CF₃ CH₂CH₂CF₂CF₂CF₂CF₃CONH(CH₃) H CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₃CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃CONH(CH₃) CH₂CH₃ CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃CONH(CH₃) F CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) F CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃CONH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CONH(CH₃) ClCF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₃ CH₂CH₂CF₂CF₂CF₂CF₃CON(CH₃)₂ H CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃

TABLE 26 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃ CH₂CH₂CF₂CF₂CF₂CF₃CON(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ ClCF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ CON(CH₃)₂Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)OCH₃ H CF₃ CH₂CH₂CF₂CF₃ C(S)OCH₃ H CF₂CF₃CH₂CH₂CF₂CF₃ C(S)OCH₃ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)OCH₃ CH₃ CF₃CH₂CH₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₃ C(S)OCH₃ F CF₃ CH₂CH₂CF₂CF₃ C(S)OCH₃ F CF₂CF₃ CH₂CH₂CF₂CF₃C(S)OCH₃ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)OCH₃ Cl CF₃ CH₂CH₂CF₂CF₃ C(S)OCH₃Cl CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂ H CF₃CH₂CH₂CF₂CF₃ C(S)NH₂ H CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂ H CF₂CF₂CF₃

TABLE 27 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₃ C(S)NH₂ CH₃ CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂CH₂CH₃ CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂ F CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂ FCF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂ Cl CF₃CH₂CH₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃CH₂CH₂CF₂CF₃ C(S)NH(CH₃) H CF₃ CH₂CH₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₃CH₂CH₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₃CH₂CH₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH(CH₃) CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃ CH₂CH₂CF₂CF₃ C(S)NH(CH₃)CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃C(S)NH(CH₃) F CF₃ CH₂CH₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₃ CH₂CH₂CF₂CF₃C(S)NH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH(CH₃) Cl CF₃ CH₂CH₂CF₂CF₃C(S)NH(CH₃) Cl CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₂CF₃

TABLE 28 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ H CF₃ CH₂CH₂CF₂CF₃C(S)N(CH₃)₂ H CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₃C(S)N(CH₃)₂ CH₃ CF₃ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃C(S)N(CH₃)₂ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₃CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ F CF₃ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ FCF₂CF₃ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ ClCF₃ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ ClCF₂CF₂CF₃ CH₂CH₂CF₃ C(S)OCH₃ H CF₃ CH₂CH₂CF₃ C(S)OCH₃ H CF₂CF₃ CH₂CH₂CF₃C(S)OCH₃ H CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)OCH₃ CH₃ CF₃ CH₂CH₂CF₃ C(S)OCH₃ CH₃CF₂CF₃ CH₂CH₂CF₃ C(S)OCH₃ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)OCH₃ F CF₃CH₂CH₂CF₃ C(S)OCH₃ F CF₂CF₃ CH₂CH₂CF₃ C(S)OCH₃ F CF₂CF₂CF₃ CH₂CH₂CF₃C(S)OCH₃ Cl CF₃ CH₂CH₂CF₃ C(S)OCH₃ Cl CF₂CF₃ CH₂CH₂CF₃ C(S)OCH₃ ClCF₂CF₂CF₃

TABLE 29 R¹ R² R³ R⁴ CH₂CH₂CF₃ C(S)NH₂ H CF₃ CH₂CH₂CF₃ C(S)NH₂ H CF₂CF₃CH₂CH₂CF₃ C(S)NH₂ H CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)NH₂ CH₃ CF₃ CH₂CH₂CF₃C(S)NH₂ CH₃ CF₂CF₃ CH₂CH₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)NH₂CH₂CH₃ CF₃ CH₂CH₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₃ C(S)NH₂ CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)NH₂ F CF₃ CH₂CH₂CF₃ C(S)NH₂ F CF₂CF₃ CH₂CH₂CF₃C(S)NH₂ F CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)NH₂ Cl CF₃ CH₂CH₂CF₃ C(S)NH₂ Cl CF₂CF₃CH₂CH₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)NH(CH₃) H CF₃ CH₂CH₂CF₃C(S)NH(CH₃) H CF₂CF₃ CH₂CH₂CF₃ C(S)NH(CH₃) H CF₂CF₂CF₃ CH₂CH₂CF₃C(S)NH(CH₃) CH₃ CF₃ CH₂CH₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃ CH₂CH₂CF₃C(S)NH(CH₃) CH₃ CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃ CH₂CH₂CF₃C(S)NH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CH₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₃ C(S)NH(CH₃) F CF₃ CH₂CH₂CF₃ C(S)NH(CH₃) F CF₂CF₃ CH₂CH₂CF₃C(S)NH(CH₃) F CF₂CF₂CF₃

TABLE 30 R¹ R² R³ R⁴ CH₂CH₂CF₃ C(S)NH(CH₃) Cl CF₃ CH₂CH₂CF₃ C(S)NH(CH₃)Cl CF₂CF₃ CH₂CH₂CF₃ C(S)NH(CH₃) Cl CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)N(CH₃)₂ H CF₃CH₂CH₂CF₃ C(S)N(CH₃)₂ H CF₂CF₃ CH₂CH₂CF₃ C(S)N(CH₃)₂ H CF₂CF₂CF₃CH₂CH₂CF₃ C(S)N(CH₃)₂ CH₃ CF₃ CH₂CH₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CF₃C(S)N(CH₃)₂ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₃ CH₂CH₂CF₃C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₃ C(S)N(CH₃)₂ F CF₃ CH₂CH₂CF₃ C(S)N(CH₃)₂ F CF₂CF₃ CH₂CH₂CF₃C(S)N(CH₃)₂ F CF₂CF₂CF₃ CH₂CH₂CF₃ C(S)N(CH₃)₂ Cl CF₃ CH₂CH₂CF₃C(S)N(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₂CF₃ CH₂CF₂CF₃C(S)OCH₃ H CF₃ CH₂CF₂CF₃ C(S)OCH₃ H CF₂CF₃ CH₂CF₂CF₃ C(S)OCH₃ HCF₂CF₂CF₃ CH₂CF₂CF₃ C(S)OCH₃ CH₃ CF₃ CH₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₃CH₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ C(S)OCH₃ F CF₃ CH₂CF₂CF₃C(S)OCH₃ F CF₂CF₃ CH₂CF₂CF₃ C(S)OCH₃ F CF₂CF₂CF₃

TABLE 31 R¹ R² R³ R⁴ CH₂CF₂CF₃ C(S)OCH₃ Cl CF₃ CH₂CF₂CF₃ C(S)OCH₃ ClCF₂CF₃ CH₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₂CF₃ CH₂CF₂CF₃ C(S)NH₂ H CF₃ CH₂CF₂CF₃C(S)NH₂ H CF₂CF₃ CH₂CF₂CF₃ C(S)NH₂ H CF₂CF₂CF₃ CH₂CF₂CF₃ C(S)NH₂ CH₃ CF₃CH₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₃ CH₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃C(S)NH₂ CH₂CH₃ CF₃ CH₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₃ CH₂CF₂CF₃ C(S)NH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ C(S)NH₂ F CF₃ CH₂CF₂CF₃ C(S)NH₂ F CF₂CF₃CH₂CF₂CF₃ C(S)NH₂ F CF₂CF₂CF₃ CH₂CF₂CF₃ C(S)NH₂ Cl CF₃ CH₂CF₂CF₃ C(S)NH₂Cl CF₂CF₃ CH₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃ CH₂CF₂CF₃ C(S)NH(CH₃) H CF₃CH₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₃ CH₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₂CF₃CH₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₃ CH₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃ CH₂CF₂CF₃C(S)NH(CH₃) CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃ CH₂CF₂CF₃C(S)NH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃

TABLE 32 R¹ R² R³ R⁴ CH₂CF₂CF₃ C(S)NH(CH₃) F CF₃ CH₂CF₂CF₃ C(S)NH(CH₃) FCF₂CF₃ CH₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₂CF₃ CH₂CF₂CF₃ C(S)NH(CH₃) Cl CF₃CH₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₃ CH₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₂CF₃CH₂CF₂CF₃ C(S)N(CH₃)₂ H CF₃ CH₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₃ CH₂CF₂CF₃C(S)N(CH₃)₂ H CF₂CF₂CF₃ CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₃ CH₂CF₂CF₃C(S)N(CH₃)₂ CH₃ CF₂CF₃ CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃C(S)N(CH₃)₂ CH₂CH₃ CF₃ CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CF₂CF₃C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₃ C(S)N(CH₃)₂ F CF₃ CH₂CF₂CF₃C(S)N(CH₃)₂ F CF₂CF₃ CH₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₂CF₃ CH₂CF₂CF₃C(S)N(CH₃)₂ Cl CF₃ CH₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₃ CH₂CF₂CF₃ C(S)N(CH₃)₂Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)OCH₃ H CF₃ CH₂CF₂CF₂CF₃ C(S)OCH₃ H CF₂CF₃CH₂CF₂CF₂CF₃ C(S)OCH₃ H CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₃CH₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₂CF₃

TABLE 33 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₃ C(S)OCH₃ F CF₃ CH₂CF₂CF₂CF₃ C(S)OCH₃ FCF₂CF₃ CH₂CF₂CF₂CF₃ C(S)OCH₃ F CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₃CH₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₂CF₃CH₂CF₂CF₂CF₃ C(S)NH₂ H CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂ H CF₂CF₃ CH₂CF₂CF₂CF₃C(S)NH₂ H CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂CH₂CH₃ CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂ F CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂ FCF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂ F CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₃CH₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃CH₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₃ CH₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₃CH₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₃CH₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃CF₂CF₂CF₃

TABLE 34 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃ CH₂CF₂CF₂CF₃C(S)NH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃CH₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₃ CH₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₃CH₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₃CH₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₂CF₃CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₃ CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₃CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₃CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₃ CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₃C(S)N(CH₃)₂ F CF₃ CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₃ CH₂CF₂CF₂CF₃C(S)N(CH₃)₂ F CF₂CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₃ CH₂CF₂CF₂CF₃C(S)N(CH₃)₂ Cl CF₂CF₃ CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ H CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ H CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ H CF₂CF₂CF₃

TABLE 35 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃C(S)OCH₃ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ F CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ F CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₃CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ H CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ H CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ F CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ F CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ F CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) HCF₂CF₂CF₃

TABLE 36 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃C(S)NH(CH₃) CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃)CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) FCF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) FCF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃)Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃C(S)N(CH₃)₂ H CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₃ CH₂CH₂CF₂CF₂CF₃C(S)N(CH₃)₂ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₃CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₃ CH₂CH₂CF₂CF₂CF₃C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₃CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₂CF₃

TABLE 37 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₃ CH₂CH₂CF₂CF₂CF₃C(S)N(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ H CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ H CF₂CF₃CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ H CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ CH₃ CF₃CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ CH₃CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ F CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ FCF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ F CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃Cl CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ Cl CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)OCH₃ ClCF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ H CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ HCF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ H CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ CH₃CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ CH₃CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ CH₂CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂HC(S)NH₂ F CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ F CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂F CF₂CF₂CF₃

TABLE 38 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ Cl CF₃ CH₂CF₂CF₂CF₂CF₂HC(S)NH₂ Cl CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH₂ Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂HC(S)NH(CH₃) H CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) H CF₂CF₃ CH₂CF₂CF₂CF₂CF₂HC(S)NH(CH₃) H CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) CH₃ CF₃CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) CH₃CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) CH₂CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂HC(S)NH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) F CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) F CF₂CF₃CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) F CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) ClCF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃) Cl CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)NH(CH₃)Cl CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ H CF₃ CH₂CF₂CF₂CF₂CF₂HC(S)N(CH₃)₂ H CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ H CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ CH₃CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ CH₃ CF₂CF₂CF₃ CH₂CF₂CF₂CF₂CF₂HC(S)N(CH₃)₂ CH₂CH₃ CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₃CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃

TABLE 39 R¹ R² R³ R⁴ CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ F CF₃ CH₂CF₂CF₂CF₂CF₂HC(S)N(CH₃)₂ F CF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ F CF₂CF₂CF₃CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ Cl CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ ClCF₂CF₃ CH₂CF₂CF₂CF₂CF₂H C(S)N(CH₃)₂ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)OCH₃ H CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)OCH₃ H CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)OCH₃ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)OCH₃ F CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)OCH₃F CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)OCH₃ F CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)OCH₃ Cl CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)OCH₃ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ H CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ H CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ HCF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)NH₂ CH₂CH₃ CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₂CF₃

TABLE 40 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ F CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)NH₂ F CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ F CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) HCF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)NH(CH₃) H CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃)CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) FCF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)NH(CH₃) Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ HCF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)N(CH₃)₂ CH₃ CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₂CF₃

TABLE 41 R¹ R² R³ R⁴ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₃CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ FCF₂CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₃ CH₂CH₂CF₂CF₂CF₂CF₃C(S)N(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₂CF₃

TABLE 42 R¹ R² R³ R⁴ CF₂CF₂CF₃ CN H CF₃ CF₂CF₂CF₃ CN H CF₂CF₃ CF₂CF₂CF₃CN H CF₂CF₂CF₃ CF₂CF₂CF₃ CN CH₃ CF₃ CF₂CF₂CF₃ CN CH₃ CF₂CF₃ CF₂CF₂CF₃ CNCH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ CN CH₂CH₃ CF₃ CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₃CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ CN CH₂CH₂CH₃ CF₃ CF₂CF₂CF₃ CNCH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₃ CN CH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ CN CH(CH₃)₂CF₃ CF₂CF₂CF₃ CN CH(CH₃)₂ CF₂CF₃ CF₂CF₂CF₃ CN CH(CH₃)₂ CF₂CF₂CF₃CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₃ CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₃CN CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₃ CF₂CF₂CF₃ CNCH₂CH₂CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃CN F CF₃ CF₂CF₂CF₃ CN F CF₂CF₃ CF₂CF₂CF₃ CN F CF₂CF₂CF₃ CF₂CF₂CF₃ CN ClCF₃ CF₂CF₂CF₃ CN Cl CF₂CF₃ CF₂CF₂CF₃ CN Cl CF₂CF₂CF₃

TABLE 43 R¹ R² R³ R⁴ CF₂CF₂CF₃ CO₂CH₃ H CF₃ CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₃CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₃ CF₂CF₂CF₃ CO₂CH₃CH₃ CF₂CF₃ CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₃CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₃ CF₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₃CF₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ CO₂CH₃ F CF₃ CF₂CF₂CF₃CO₂CH₃ F CF₂CF₃ CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CF₂CF₂CF₃ CO₂CH₃ Cl CF₃CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃ CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃ CF₂CF₂CF₃CO₂C(CH₃)₃ H CF₃ CF₂CF₂CF₃ CO₂C(CH₃)₃ H CF₂CF₃ CF₂CF₂CF₃ CO₂C(CH₃)₃ HCF₂CF₂CF₃ CF₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₃ CF₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₂CF₃CF₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ CO₂C(CH₃)₃ F CF₃ CF₂CF₂CF₃CO₂C(CH₃)₃ F CF₂CF₃ CF₂CF₂CF₃ CO₂C(CH₃)₃ F CF₂CF₂CF₃

TABLE 44 R¹ R² R³ R⁴ CF₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₃ CF₂CF₂CF₃ CO₂C(CH₃)₃ ClCF₂CF₃ CF₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₂CF₂CF₃ CF₂CF₂CF₃ CONH₂ H CF₃ CF₂CF₂CF₃CONH₂ H CF₂CF₃ CF₂CF₂CF₃ CONH₂ H CF₂CF₂CF₃ CF₂CF₂CF₃ CONH₂ CH₃ CF₃CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₃ CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ CONH₂CH₂CH₃ CF₃ CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₃ CONH₂ CH₂CH₃CF₂CF₂CF₃ CF₂CF₂CF₃ CONH₂ F CF₃ CF₂CF₂CF₃ CONH₂ F CF₂CF₃ CF₂CF₂CF₃ CONH₂F CF₂CF₂CF₃ CF₂CF₂CF₃ CONH₂ Cl CF₃ CF₂CF₂CF₃ CONH₂ Cl CF₂CF₃ CF₂CF₂CF₃CONH₂ Cl CF₂CF₂CF₃ CF₂CF₂CF₃ CONH(CH₃) H CF₃ CF₂CF₂CF₃ CONH(CH₃) HCF₂CF₃ CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₂CF₃ CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₃CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₃ CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₃ CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₂CF₃

TABLE 45 R¹ R² R³ R⁴ CF₂CF₂CF₃ CONH(CH₃) F CF₃ CF₂CF₂CF₃ CONH(CH₃) FCF₂CF₃ CF₂CF₂CF₃ CONH(CH₃) F CF₂CF₂CF₃ CF₂CF₂CF₃ CONH(CH₃) Cl CF₃CF₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₃ CF₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₂CF₃ CF₂CF₂CF₃CONH(CH₂CH₃) H CF₃ CF₂CF₂CF₃ CONH(CH₂CH₃) H CF₂CF₃ CF₂CF₂CF₃CONH(CH₂CH₃) H CF₂CF₂CF₃ CF₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₃ CF₂CF₂CF₃CONH(CH₂CH₃) CH₃ CF₂CF₃ CF₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃CONH(CH₂CH₃) CH₂CH₃ CF₃ CF₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₂CF₃ CF₂CF₂CF₃CONH(CH₂CH₃) CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ CONH(CH₂CH₃) F CF₃ CF₂CF₂CF₃CONH(CH₂CH₃) F CF₂CF₃ CF₂CF₂CF₃ CONH(CH₂CH₃) F CF₂CF₂CF₃ CF₂CF₂CF₃CONH(CH₂CH₃) Cl CF₃ CF₂CF₂CF₃ CONH(CH₂CH₃) Cl CF₂CF₃ CF₂CF₂CF₃CONH(CH₂CH₃) Cl CF₂CF₂CF₃ CF₂CF₂CF₃ CON(CH₃)₂ H CF₃ CF₂CF₂CF₃ CON(CH₃)₂H CF₂CF₃ CF₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃ CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₃CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₂CF₃

TABLE 46 R¹ R² R³ R⁴ CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃ CF₂CF₂CF₃ CON(CH₃)₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ CON(CH₃)₂ FCF₃ CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₃ CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₃ CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₃ CF₂CF₂CF₃CON(CH₃)₂ Cl CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)OCH₃ H CF₃ CF₂CF₂CF₃ C(S)OCH₃ HCF₂CF₃ CF₂CF₂CF₃ C(S)OCH₃ H CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₃CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₃ CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃C(S)OCH₃ F CF₃ CF₂CF₂CF₃ C(S)OCH₃ F CF₂CF₃ CF₂CF₂CF₃ C(S)OCH₃ FCF₂CF₂CF₃ CF₂CF₂CF₃ C(S)OCH₃ Cl CF₃ CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₃CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)NH₂ H CF₃ CF₂CF₂CF₃C(S)NH₂ H CF₂CF₃ CF₂CF₂CF₃ C(S)NH₂ H CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₃CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₃ CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃

TABLE 47 R¹ R² R³ R⁴ CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₃ CF₂CF₂CF₃ C(S)NH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)NH₂ F CF₃CF₂CF₂CF₃ C(S)NH₂ F CF₂CF₃ CF₂CF₂CF₃ C(S)NH₂ F CF₂CF₂CF₃ CF₂CF₂CF₃C(S)NH₂ Cl CF₃ CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₃ CF₂CF₂CF₃ C(S)NH₂ ClCF₂CF₂CF₃ CF₂CF₂CF₃ C(S)NH(CH₃) H CF₃ CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₃CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₃CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃ CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₂CF₃CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃ CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₃CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)NH(CH₃) F CF₃CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₃ CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₂CF₃CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₃ CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₃ CF₂CF₂CF₃C(S)NH(CH₃) Cl CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₃ CF₂CF₂CF₃C(S)N(CH₃)₂ H CF₂CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₂CF₃

TABLE 48 R¹ R² R³ R⁴ CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂CH₃ CF₂CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂CH₂CH₃ CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂ FCF₂CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₂CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₃CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₃ CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₂CF₃

TABLE 49 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₃ CN H CF₃ CF₂CF₂CF₂CF₃ CN H CF₂CF₃CF₂CF₂CF₂CF₃ CN H CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CN CH₃ CF₃ CF₂CF₂CF₂CF₃ CN CH₃CF₂CF₃ CF₂CF₂CF₂CF₃ CN CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₃CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₃ CF₃ CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₃ CF₂CF₃CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CN CH(CH₃)₂ CF₃CF₂CF₂CF₂CF₃ CN CH(CH₃)₂ CF₂CF₃ CF₂CF₂CF₂CF₃ CN CH(CH₃)₂ CF₂CF₂CF₃CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₃ CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₂CF₃CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃CF₃ CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CNCH₂CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CN F CF₃ CF₂CF₂CF₂CF₃ CN F CF₂CF₃CF₂CF₂CF₂CF₃ CN F CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CN Cl CF₃ CF₂CF₂CF₂CF₃ CN ClCF₂CF₃ CF₂CF₂CF₂CF₃ CN Cl CF₂CF₂CF₃

TABLE 50 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ HCF₂CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₃CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₂CF₃CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₃CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₃CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₃ CF₂CF₂CF₂CF₃CO₂CH₃ Cl CF₂CF₃ CF₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ H CF₃ CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ H CF₂CF₃ CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₃ CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ F CF₃ CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ F CF₂CF₃ CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ F CF₂CF₂CF₃

TABLE 51 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₃ CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ Cl CF₂CF₃ CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₃CONH₂ H CF₃ CF₂CF₂CF₂CF₃ CONH₂ H CF₂CF₃ CF₂CF₂CF₂CF₃ CONH₂ H CF₂CF₂CF₃CF₂CF₂CF₂CF₃ CONH₂ CH₃ CF₃ CF₂CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃CONH₂ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₃ CF₂CF₂CF₂CF₃ CONH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CONH₂ FCF₃ CF₂CF₂CF₂CF₃ CONH₂ F CF₂CF₃ CF₂CF₂CF₂CF₃ CONH₂ F CF₂CF₂CF₃CF₂CF₂CF₂CF₃ CONH₂ Cl CF₃ CF₂CF₂CF₂CF₃ CONH₂ Cl CF₂CF₃ CF₂CF₂CF₂CF₃CONH₂ Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₃) H CF₃ CF₂CF₂CF₂CF₃ CONH(CH₃) HCF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₃CF₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₃ CF₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃CF₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₂CF₃

TABLE 52 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₃ CONH(CH₃) F CF₃ CF₂CF₂CF₂CF₃ CONH(CH₃)F CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₃) F CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₃) ClCF₃ CF₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₂CF₃CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) H CF₃ CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) H CF₂CF₃CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) H CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₃CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₃CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₃ CF₂CF₂CF₂CF₃ CONH(CH₂CH₃)CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃CONH(CH₂CH₃) F CF₃ CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) F CF₂CF₃ CF₂CF₂CF₂CF₃CONH(CH₂CH₃) F CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) Cl CF₃ CF₂CF₂CF₂CF₃CONH(CH₂CH₃) Cl CF₂CF₃ CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) Cl CF₂CF₂CF₃CF₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₃ CF₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₃CF₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₃CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₂CF₃

TABLE 53 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃ CF₂CF₂CF₂CF₃CON(CH₃)₂ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₃ CF₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₃CF₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₃CF₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₃ CF₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₂CF₃CF₂CF₂CF₂CF₃ C(S)OCH₃ H CF₃ CF₂CF₂CF₂CF₃ C(S)OCH₃ H CF₂CF₃ CF₂CF₂CF₂CF₃C(S)OCH₃ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₃ CF₂CF₂CF₂CF₃ C(S)OCH₃CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)OCH₃ FCF₃ CF₂CF₂CF₂CF₃ C(S)OCH₃ F CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)OCH₃ F CF₂CF₂CF₃CF₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₃ CF₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₃CF₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH₂ H CF₃CF₂CF₂CF₂CF₃ C(S)NH₂ H CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH₂ H CF₂CF₂CF₃CF₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₃ CF₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₃CF₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃

TABLE 54 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₃ CF₂CF₂CF₂CF₃C(S)NH₂ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃C(S)NH₂ F CF₃ CF₂CF₂CF₂CF₃ C(S)NH₂ F CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH₂ FCF₂CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₃ CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₃CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₃CF₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₂CF₃CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃)CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃)F CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃)Cl CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)NH(CH₃) ClCF₂CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₃ CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ HCF₂CF₃ CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₂CF₃

TABLE 55 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₃ CF₂CF₂CF₂CF₃C(S)N(CH₃)₂ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₃ CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₃C(S)N(CH₃)₂ F CF₃ CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₃ CF₂CF₂CF₂CF₃C(S)N(CH₃)₂ F CF₂CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₃ CF₂CF₂CF₂CF₃C(S)N(CH₃)₂ Cl CF₂CF₃ CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₂CF₃

TABLE 56 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₃ CN H CF₃ CF₂CF₂CF₂CF₂CF₃ CN HCF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN CH₃ CF₃CF₂CF₂CF₂CF₂CF₃ CN CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₃ CF₃CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₃CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN CH(CH₃)₂ CF₃ CF₂CF₂CF₂CF₂CF₃ CN CH(CH₃)₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN CH(CH₃)₂ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CNCH₂CH₂CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃CN CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₃CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CNCH₂CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN F CF₃ CF₂CF₂CF₂CF₂CF₃ CN FCF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN Cl CF₃CF₂CF₂CF₂CF₂CF₃ CN Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CN Cl CF₂CF₂CF₃

TABLE 57 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃H CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃CO₂CH₃ CH₂CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₃CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ H CF₃CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ H CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ HCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ F CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ F CF₂CF₃ CF₂CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ F CF₂CF₂CF₃

TABLE 58 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₃ CF₂CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH₂ H CF₃ CF₂CF₂CF₂CF₂CF₃ CONH₂ H CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH₂ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₃ CF₃CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH₂ F CF₃CF₂CF₂CF₂CF₂CF₃ CONH₂ F CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH₂ F CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH₂ Cl CF₃ CF₂CF₂CF₂CF₂CF₃ CONH₂ Cl CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH₂ Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) H CF₃CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₃)CH₂CH₃ CF₂CF₂CF₃

TABLE 59 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) F CF₃ CF₂CF₂CF₂CF₂CF₃CONH(CH₃) F CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃CONH(CH₃) Cl CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₃CONH(CH₃) Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) H CF₃CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) H CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) HCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃CONH(CH₂CH₃) CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃)CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) F CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) F CF₂CF₃CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) ClCF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃)Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ HCF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂CH₃ CF₂CF₂CF₃

TABLE 60 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ FCF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂Cl CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ ClCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ H CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ HCF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ F CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ FCF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ ClCF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ ClCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ H CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ H CF₂CF₃CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₃CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃

TABLE 61 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃C(S)NH₂ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ F CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ F CF₂CF₃CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₃CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₃CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃)CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃C(S)NH(CH₃) CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₃CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) ClCF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) ClCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂H CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₂CF₃

TABLE 62 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃C(S)N(CH₃)₂ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₃CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ ClCF₃ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ ClCF₂CF₂CF₃

TABLE 63 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₂CF₃ CN H CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN HCF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₃CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CNCH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN CH(CH₃)₂ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CN CH(CH₃)₂ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN CH(CH₃)₂CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CNCH₂CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CNCH₂CH₂CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CN F CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN F CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CN F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN Cl CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CN Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CN Cl CF₂CF₂CF₃

TABLE 64 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CO₂CH₃ H CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CO₂CH₃ CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CO₂CH₃ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₃CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CO₂CH₃ CH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂CH₃ ClCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ H CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ H CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ H CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ CH₃CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CO₂C(CH₃)₃ F CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ F CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ F CF₂CF₂CF₃

TABLE 65 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CO₂C(CH³)₃ Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CO₂C(CH³)₃ ClCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ H CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ HCF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₃CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₃CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ F CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ F CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ Cl CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH₂ Cl CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) H CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃)CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CONH(CH₃) CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃)CH₂CH₃ CF₂CF₂CF₃

TABLE 66 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) F CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) F CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) FCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CONH(CH₃) Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) H CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) HCF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CONH(CH₂CH₃) CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CONH(CH₂CH₃) CH₂CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CONH(CH₂CH₃) F CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) F CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CONH(CH₂CH₃) Cl CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) Cl CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CONH(CH₂CH₃) Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CON(CH₃)₂ H CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CON(CH₃)₂ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₃CF₂CF₂CF₃

TABLE 67 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₃ CF₂CF₂CF₂CF₂CF₂CF₃CON(CH₃)₂ F CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ ClCF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃C(S)OCH₃ H CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ H CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃C(S)OCH₃ H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ CH₃CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ F CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃F CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ F CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃C(S)OCH₃ Cl CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃C(S)OCH₃ Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ H CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ H CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ HCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃

TABLE 68 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ F CF₃ CF₂CF₂CF₂CF₂CF₂CF₃C(S)NH₂ F CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ F CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) HCF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃C(S)NH(CH₃) H CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃)CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) FCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₃ CF₂CF₂CF₂CF₂CF₂CF₃C(S)NH(CH₃) Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₂CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ HCF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₂CF₃

TABLE 69 R¹ R² R³ R⁴ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₃CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ FCF₂CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₃ CF₂CF₂CF₂CF₂CF₂CF₃C(S)N(CH₃)₂ Cl CF₂CF₃ CF₂CF₂CF₂CF₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₂CF₃

TABLE 70 R¹ R² R³ R⁴ CH₂CH₂CH₂CH₂CF₃ CN H CF₃ CH₂CH₂CH₂CH₂CF₃ CN HCF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN H CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN CH₃ CF₃CH₂CH₂CH₂CH₂CF₃ CN CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CN CH₂CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃ CN CH₂CH₃ CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN CH₂CH₂CH₃ CF₃CH₂CH₂CH₂CH₂CF₃ CN CH₂CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN CH₂CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN CH(CH₃)₂ CF₃ CH₂CH₂CH₂CH₂CF₃ CN CH(CH₃)₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN CH(CH₃)₂ CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CNCH₂CH₂CH₂CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃ CN CH₂CH₂CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃CN CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₃CH₂CH₂CH₂CH₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CNCH₂CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN F CF₃ CH₂CH₂CH₂CH₂CF₃ CN FCF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN F CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN Cl CF₃CH₂CH₂CH₂CH₂CF₃ CN Cl CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CN Cl CF₂CF₂CF₃

TABLE 71 R¹ R² R³ R⁴ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ H CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃H CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ CH₃CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ CH₃CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ CH₂CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃CO₂CH₃ CH₂CH₂CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ F CF₃CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ F CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ F CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ Cl CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ Cl CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂C(CH₃)₃ H CF₃CH₂CH₂CH₂CH₂CF₃ CO₂C(CH₃)₃ H CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂C(CH₃)₃ HCF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂C(CH₃)₃ CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂C(CH₃)₃CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂C(CH₃)₃ CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃CO₂C(CH₃)₃ F CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂C(CH₃)₃ F CF₂CF₃ CH₂CH₂CH₂CH₂CF₃CO₂C(CH₃)₃ F CF₂CF₂CF₃

TABLE 72 R¹ R² R³ R⁴ CH₂CH₂CH₂CH₂CF₃ CO₂C(CH₃)₃ Cl CF₃ CH₂CH₂CH₂CH₂CF₃CO₂C(CH₃)₃ Cl CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CO₂C(CH₃)₃ Cl CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH₂ H CF₃ CH₂CH₂CH₂CH₂CF₃ CONH₂ H CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH₂ H CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH₂ CH₃ CF₃CH₂CH₂CH₂CH₂CF₃ CONH₂ CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH₂ CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH₂ CH₂CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃ CONH₂ CH₂CH₃ CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH₂ F CF₃CH₂CH₂CH₂CH₂CF₃ CONH₂ F CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH₂ F CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH₂ Cl CF₃ CH₂CH₂CH₂CH₂CF₃ CONH₂ Cl CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH₂ Cl CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) H CF₃CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) H CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) H CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) CH₃ CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) CH₂CH₃CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₃)CH₂CH₃ CF₂CF₂CF₃

TABLE 73 R¹ R² R³ R⁴ CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) F CF₃ CH₂CH₂CH₂CH₂CF₃CONH(CH₃) F CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃CONH(CH₃) Cl CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₃) Cl CF₂CF₃ CH₂CH₂CH₂CH₂CF₃CONH(CH₃) Cl CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) H CF₃CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) H CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) HCF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃CONH(CH₂CH₃) CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃)CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) F CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) F CF₂CF₃CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) F CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) ClCF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃) Cl CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CONH(CH₂CH₃)Cl CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ H CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ HCF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂CH₃ CF₂CF₂CF₃

TABLE 74 R¹ R² R³ R⁴ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ F CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ FCF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂Cl CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ CON(CH₃)₂ ClCF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ H CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ HCF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ H CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ CH₃CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ CH₃CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ F CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ FCF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ F CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ ClCF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ Cl CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)OCH₃ ClCF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ H CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ H CF₂CF₃CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ H CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ CH₃ CF₃CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃

TABLE 75 R¹ R² R³ R⁴ CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ CH₂CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃C(S)NH₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ F CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ F CF₂CF₃CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ F CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ Cl CF₃CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ Cl CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) H CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) H CF₂CF₃CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) H CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) CH₃CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃)CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃C(S)NH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) F CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) F CF₂CF₃CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) ClCF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) Cl CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)NH(CH₃) ClCF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ H CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂H CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ H CF₂CF₂CF₃

TABLE 76 R¹ R² R³ R⁴ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃C(S)N(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ F CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ F CF₂CF₃CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ F CF₂CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ ClCF₃ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CH₂CH₂CF₃ C(S)N(CH₃)₂ ClCF₂CF₂CF₃

TABLE 77 R¹ R² R³ R⁴ CH₂CH₂CH₂CF₂CF₃ CN H CF₃ CH₂CH₂CH₂CF₂CF₃ CN HCF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN H CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN CH₃ CF₃CH₂CH₂CH₂CF₂CF₃ CN CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CN CH₂CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃ CN CH₂CH₃ CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CN CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₃ CF₃CH₂CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN CH(CH₃)₂ CF₃ CH₂CH₂CH₂CF₂CF₃ CN CH(CH₃)₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN CH(CH₃)₂ CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CNCH₂CH₂CH₂CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃CN CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₃CH₂CH₂CH₂CF₂CF₃ CN CH₂CH₂CH₂CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CNCH₂CH₂CH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN F CF₃ CH₂CH₂CH₂CF₂CF₃ CN FCF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN F CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN Cl CF₃CH₂CH₂CH₂CF₂CF₃ CN Cl CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CN Cl CF₂CF₂CF₃

TABLE 78 R¹ R² R³ R⁴ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ H CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃H CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ H CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ CH₃CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ CH₃CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃CO₂CH₃ CH₂CH₂CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ CH₂CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ F CF₃CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ F CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ F CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ Cl CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CO₂CH₃ Cl CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ H CF₃CH₂CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ H CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ HCF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃CO₂C(CH₃)₃ F CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ F CF₂CF₃ CH₂CH₂CH₂CF₂CF₃CO₂C(CH₃)₃ F CF₂CF₂CF₃

TABLE 79 R¹ R² R³ R⁴ CH₂CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₃ CH₂CH₂CH₂CF₂CF₃CO₂C(CH₃)₃ Cl CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CO₂C(CH₃)₃ Cl CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH₂ H CF₃ CH₂CH₂CH₂CF₂CF₃ CONH₂ H CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH₂ H CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH₂ CH₃ CF₃CH₂CH₂CH₂CF₂CF₃ CONH₂ CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH₂ CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH₂ CH₂CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH₂ CH₂CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH₂ F CF₃CH₂CH₂CH₂CF₂CF₃ CONH₂ F CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH₂ F CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH₂ Cl CF₃ CH₂CH₂CH₂CF₂CF₃ CONH₂ Cl CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH₂ Cl CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) H CF₃CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) H CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) H CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) CH₂CH₃CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₃)CH₂CH₃ CF₂CF₂CF₃

TABLE 80 R¹ R² R³ R⁴ CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) F CF₃ CH₂CH₂CH₂CF₂CF₃CONH(CH₃) F CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃CONH(CH₃) Cl CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₃) Cl CF₂CF₃ CH₂CH₂CH₂CF₂CF₃CONH(CH₃) Cl CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) H CF₃CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) H CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) HCF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃CONH(CH₂CH₃) CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃)CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) F CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) F CF₂CF₃CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) F CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) ClCF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃) Cl CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CONH(CH₂CH₃)Cl CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ H CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ HCF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ H CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂CH₃ CF₂CF₂CF₃

TABLE 81 R¹ R² R³ R⁴ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₃CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ CH₂CH₃CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ F CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ FCF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ F CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂Cl CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ CON(CH₃)₂ ClCF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ H CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ HCF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ H CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ CH₃CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ CH₃CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ F CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ FCF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ F CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ ClCF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ Cl CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)OCH₃ ClCF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ H CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ H CF₂CF₃CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ H CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ CH₃ CF₃CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ CH₃ CF₂CF₂CF₃

TABLE 82 R¹ R² R³ R⁴ CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃C(S)NH₂ CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ F CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ F CF₂CF₃CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ F CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ Cl CF₃CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH₂ Cl CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) H CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₃CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) H CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) CH₃CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃)CH₃ CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃C(S)NH(CH₃) CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) F CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₃CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) F CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) ClCF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) Cl CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)NH(CH₃) ClCF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ H CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂H CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ H CF₂CF₂CF₃

TABLE 83 R¹ R² R³ R⁴ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃C(S)N(CH₃)₂ CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂CH₂CH₃ CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ CH₂CH₃ CF₂CF₂CF₃CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ F CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₃CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ F CF₂CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ ClCF₃ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ Cl CF₂CF₃ CH₂CH₂CH₂CF₂CF₃ C(S)N(CH₃)₂ ClCF₂CF₂CF₃

The compound given by the formula (I-B);

wherein R¹, R², R³ and R⁴ are the combination described in Table 1 toTable 83.

The compound given by the formula (I-C);

wherein R¹, R², R³ and R⁴ are the combination described in Table 1 toTable 83.

Next, the production of intermediate of the present compound will beillustrated by Reference Production Examples.

Reference Production Example 1

9.6 g of 1-bromo-3,3,3-trifluoropropane and 5 g of thiobenzoic acid weredissolved to 30 ml of N,N-dimethylformamide, and 1.45 g of sodiumhydride (60% in oil) was added thereto under ice cooling. The mixturewas stirred at room temperature for 12 hours. 10% hydrochloric acid wasadded to the reaction mixture and the mixture was extracted by ethylacetate. The organic layer was washed respectively with 10% hydrochloricacid and saturated aqueous solution of sodium chloride, dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theresidue was subjected to silica gel chromatography to obtain 6.90 g ofS-(3,3,3-trifluoropropyl)benzenethioate given by the below formula:

¹H-NMR (CDCl₃₁, TMS): δ (ppm) 7.97 (d, 2H), 7.58-7.62 (m, 1H), 7.47 (dd,2H), 3.24 (t, 2H), 2.44-2.56 (m, 2H)

Reference Production Example 2

9.9 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 5 g of thiobenzoic acidwere dissolved to 30 ml of N,N-dimethylformamide, and 5.0 g of potassiumcarbonate was added thereto under ice cooling. The mixture was stirredat room temperature for 20 hours. 10% hydrochloric acid was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed respectively with 10% hydrochloric acid andsaturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The residuewas subjected to silica gel chromatography to obtain 7.90 g ofS-(3,3,4,4,4-pentafluorobutyl)benzenethioate given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 7.95 (d, 2H), 7.58-7.65 (m, 1H), 7.47 (dd,2H), 3.27 (t, 2H), 2.38-2.53 (m, 2H)

Reference Production Example 3

2.0 g of 1-iodo-3,3,4,4,5,5,5-heptafluoropentane and 0.9 g ofthiobenzoic acid were dissolved to 20 ml of N,N-dimethylformamide, and0.9 g of potassium carbonate was added thereto under ice cooling. Themixture was stirred at room temperature for 20 hours. 10% hydrochloricacid was added to the reaction mixture and the mixture was extracted byethyl acetate. The organic layer was washed respectively with 10%hydrochloric acid and saturated aqueous solution of sodium chloride,dried over anhydrous magnesium sulfate and concentrated under reducedpressure. The residue was subjected to silica gel chromatography toobtain 1.75 g of S-(3,3,4,4,5,5,5-heptafluoropentyl)benzenethioate givenby the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 7.95 (d, 2H), 7.58-7.64 (m, 1H), 7.47 (dd,2H), 3.29 (t, 2H), 2.40-2.56 (m, 2H)

Reference Production Example 4

10 g of S-(3,3,3-trifluoropropyl)benzenethioate was dissolved to 50 mlof tetrahydrofuran and 8.4 ml of sodium methoxide (28% (w/w) methanolsolution) was added thereto under ice cooling. Furthermore, 5.1 g ofbromoacetonitrile was added dropwise thereto and the mixture was stirredat room temperature for 2 hours. 10% hydrochloric acid was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed respectively with 10% hydrochloric acid andsaturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The residuewas dissolved to 40 ml of acetic acid and 20 ml of peracetic acid (32%(w/w) acetic acid solution) was added thereto under ice cooling. Thenthe mixture was stirred at 60° C. for 10 hours. The reaction mixture wasdropped to room temperature and poured into water, then extracted byethyl acetate. The organic layer was washed respectively with saturatedaqueous solution of sodium hydrogen carbonate and saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The obtained residue was subjectedto silica gel chromatography to obtain 7.04 g of(3,3,3-trifluoropropylsulfonyl)acetonitrile given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.06 (s, 2H), 3.48-3.55 (m, 2H), 2.72-2.84(m, 2H)

Reference Production Example 5

7.1 g of S-(3,3,4,4,4-pentafluorobutyl)benzenethioate was dissolved to50 ml of tetrahydrofuran and 4.9 ml of sodium methoxide (28% (w/w)methanol solution) was added thereto under ice cooling. Furthermore, 3.0g of bromoacetonitrile was added dropwise thereto and the mixture wasstirred at room temperature for 20 hours. 10% hydrochloric acid wasadded to the reaction mixture and the mixture was extracted by ethylacetate. The organic layer was washed respectively with 10% hydrochloricacid and saturated aqueous solution of sodium chloride, dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theresidue was dissolved to 40 ml of acetic acid and 20 ml of peraceticacid (32% (w/w) acetic acid solution) was added thereto under icecooling. Then the mixture was stirred at 60° C. for 8 hours. Thereaction mixture was dropped to room temperature and poured into water,then extracted by ethyl acetate. The organic layer was washedrespectively with saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride, dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theobtained residue was subjected to silica gel chromatography to obtain5.47 g of (3,3,4,4,4-pentafluorobutylsulfonyl)acetonitrile given by thebelow formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.07 (s, 2H), 3.51-3.58 (m, 2H), 2.65-2.78(m, 2H)

Reference Production Example 6

9.7 g of S-(3,3,4,4,5,5,5-heptafluoropentyl)benzenethioate was dissolvedto 30 ml of tetrahydrofuran and 5.7 ml of sodium methoxide (28% (w/w)methanol solution) was added thereto under ice cooling. Furthermore, 3.5g of bromoacetonitrile was added dropwise thereto and the mixture wasstirred at room temperature for 10 hours. 10% hydrochloric acid wasadded to the reaction mixture and the mixture was extracted by ethylacetate. The organic layer was washed respectively with 10% hydrochloricacid and saturated aqueous solution of sodium chloride, dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theresidue was dissolved to 40 ml of acetic acid and 20 ml of peraceticacid (32% (w/w) acetic acid solution) was added thereto under icecooling. Then the mixture was stirred at 60° C. for 6 hours. Thereaction mixture was dropped to room temperature and poured into water,then extracted by ethyl acetate. The organic layer was washedrespectively with saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride, dried overanhydrous magnesium sulfate and concentrated under reduced pressure. Theobtained residue was subjected to silica gel chromatography to obtain6.54 g of S-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)acetonitrile givenby the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.09 (s, 2H), 3.54-3.59 (m, 2H), 2.69-2.84(m, 2H)

Reference Production Example 7

10 g of methyl thioglycolate and 21 g of 1-iodo-3,3,3-trifluoropropanewere dissolved to 200 ml of N,N-dimethylformamide and 13 g of potassiumcarbonate was added thereto under ice cooling. The mixture was stirredat room temperature for 20 hours. 10% hydrochloric acid was added to thereaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed respectively with 10% hydrochloric acid andsaturated aqueous solution of sodium chloride, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The residuewas dissolved to 100 ml of acetic acid and 50 ml of peracetic acid (32%(w/w) acetic acid solution) was added thereto under ice cooling. Thenthe mixture was stirred at 60° C. for 16 hours. The reaction mixture wascooled to room temperature and poured into water, then extracted byethyl acetate. The organic layer was washed respectively with saturatedaqueous solution of sodium hydrogen carbonate and saturated aqueoussolution of sodium chloride, dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The obtained residue was subjectedto silica gel chromatography to obtain 14.1 g of methyl(3,3,3-trifluoropropylsulfonyl)acetate given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.05 (s, 2H), 3.84 (s, 3H), 3.49-3.57 (m,2H), 2.66-2.79 (m, 2H)

Reference Production Example 8

10 g of methyl thioglycolate and 26 g of1-iodo-3,3,4,4,4-pentafluorobutane were dissolved to 100 ml ofN,N-dimethylformamide and 13 g of potassium carbonate was added theretounder ice cooling. The mixture was stirred at room temperature for 20hours. 10% hydrochloric acid was added to the reaction mixture and themixture was extracted by ethyl acetate. The organic layer was washedrespectively with 10% hydrochloric acid and saturated aqueous solutionof sodium chloride, dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was dissolved to 100 mlof acetic acid and 50 ml of peracetic acid (32% (w/w) acetic acidsolution) was added thereto under ice cooling. Then the mixture wasstirred at 60° C. for 16 hours. The reaction mixture was cooled to roomtemperature and poured into water, then extracted by ethyl acetate. Theorganic layer was washed respectively with saturated aqueous solution ofsodium hydrogen carbonate and saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate and concentrated underreduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 23.1 g of methyl(3,3,4,4,4-pentafluorobutylsulfonyl)acetate given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.05 (s, 2H), 3.86 (s, 3H), 3.52-3.59 (m,2H), 2.59-2.75 (m, 2H)

Reference Production Example 9

5 g of methyl thioglycolate and 15 g of 1-iodo3,3,4,4,5,5,5-heptafluoropentane were dissolved to 50 ml ofN,N-dimethylformamide and 6.5 g of potassium carbonate was added theretounder ice cooling. The mixture was stirred at room temperature for 10hours. 10% hydrochloric acid was added to the reaction mixture and themixture was extracted by ethyl acetate. The organic layer was washedrespectively with 10% hydrochloric acid and saturated aqueous solutionof sodium chloride, dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was dissolved to 50 mlof acetic acid and 20 ml of peracetic acid (32% (w/w) acetic acidsolution) was added thereto under ice cooling. Then the mixture wasstirred at 60° C. for 4 hours. The reaction mixture was cooled to roomtemperature and poured into water, then extracted by ethyl acetate. Theorganic layer was washed respectively with saturated aqueous solution ofsodium hydrogen carbonate and saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate and concentrated underreduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 12.6 g of methyl(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)acetate given by the belowformula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.06 (s, 2H), 3.86 (s, 3H), 3.52-3.59 (m,2H), 2.63-2.78 (m, 2H)

Reference Production Example 10

0.3 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate wasdissolved to 30 ml of methanol. An aqueous solution of potassiumhydroxide (a mixed solution of 0.3 g of potassium hydroxide and 5 ml ofwater) was added thereto at room temperature and the mixture was stirredat the same temperature for 24 hours. 10% hydrochloric acid was added tothe reaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate and concentrated underreduced pressure to obtain 0.28 g of5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoic acidgiven by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.91-3.98 (m, 1H), 3.48-3.56 (m, 2H),2.64-2.78 (m, 2H), 2.23-2.54 (m, 4H)

Reference Production Example 11

0.5 g of methyl2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoatewas dissolved to 30 ml of methanol. An aqueous solution of potassiumhydroxide (a mixed solution of 0.3 g of potassium hydroxide and 5 ml ofwater) was added thereto at room temperature and the mixture was stirredat the same temperature for 6 hours. 10% hydrochloric acid was added tothe reaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate and concentrated underreduced pressure to obtain 0.48 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoicacid given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.48-3.54 (m, 2H), 2.67-2.78 (m, 2H),2.18-2.56 (m, 4H), 1.73 (s, 3H)

Reference Production Example 12

0.5 g of methyl2-ethyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoatewas dissolved to 30 ml of methanol. An aqueous solution of potassiumhydroxide (a mixed solution of 0.3 g of potassium hydroxide and 5 ml ofwater) was added thereto at room temperature and the mixture was stirredat the same temperature for 10 hours. 10% hydrochloric acid was added tothe reaction mixture and the mixture was extracted by ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate and concentrated underreduced pressure to obtain 0.48 g of2-ethyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoicacid given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.35-3.71 (m, 2H), 2.08-2.78 (m, 8H), 1.10(t, 3H)

Reference Production Example 13

20 g of ethyl 2-mercaptopropionate and 33 g of1-iodo-3,3,3-trifluoropropane were dissolved to 200 ml ofN,N-dimethylformamide and 21 g of potassium carbonate was added theretounder ice cooling. The mixture was stirred at room temperature for 4hours. 10% hydrochloric acid was added to the reaction mixture and themixture was extracted by ethyl acetate. The organic layer was washedrespectively with 10% hydrochloric acid and saturated aqueous solutionof sodium chloride, dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residue was dissolved to 100 mlof acetic acid and 30 ml of peracetic acid (30% (w/w) acetic acidsolution) was added thereto under ice cooling. Then the mixture wasstirred at 60° C. for 4 hours. The reaction mixture was dropped to roomtemperature and poured into water, then extracted by ethyl acetate. Theorganic layer was washed respectively with saturated aqueous solution ofsodium hydrogen carbonate and saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate and concentrated underreduced pressure. The obtained residue was subjected to silica gelchromatography to obtain 36.3 g of ethyl2-(3,3,3-trifluoropropylsulfonyl)propionate given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 4.24-4.38 (m, 2H), 3.94 (q, 1H), 3.37-3.55(m, 2H), 2.62-2.78 (m, 2H), 1.69 (d, 3H), 1.34 (t, 3H)

Referential Production Example 14

40 g of 5,5,6,6,6-pentafluorohexanenitrile was added dropwise with 11 mlof bromine and 2 ml of phosphorus tribromide at room temperature,followed by stirring at 90° C. for 6 hours. The reaction mixture wasdropped to room temperature. The reaction mixture was poured into water,followed by extraction with ethyl acetate. The organic layer wassubsequently washed with saturated aqueous solution of sodiumthiosulfate and saturated aqueous solution of sodium chloride, driedover anhydrous magnesium sulfate, and then concentrated under reducedpressure. The obtained residue was subjected to silica gelchromatography to obtain 17.5 g of2-bromo-5,5,6,6,6-pentafluorohexanenitrile given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.95-4.04 (m, 1H), 3.49-3.57 (m, 2H),2.06-2.78 (m, 6H)

Referential Production Example 15

0.5 g of methyl5,5,6,6,7,7,7-heptafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptanoatewas dissolved to 30 ml of methanol, added with an aqueous solution ofpotassium hydroxide (a mixed solution of 0.3 g of potassium hydroxideand 5 ml of water) at room temperature, and then stirred at the sametemperature for 2 days. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure to obtain 0.48 g of5,5,6,6,7,7,7-heptafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptanoicacid given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.95-4.04 (m, 1H), 3.49-3.57 (m, 2H),2.06-2.78 (m, 6H)

Referential Production Example 16

1.2 g of methyl5,5,6,6,7,7,7-heptafluoro-2-methyl-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptanoatewas dissolved to 30 ml of methanol, added with an aqueous solution ofpotassium hydroxide (a mixed solution of 0.8 g of potassium hydroxideand 10 ml of water) at room temperature, and then stirred at the sametemperature for 2 days. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure to obtain 1.10 g of5,5,6,6,7,7,7-heptafluoro-2-methyl-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptanoicacid given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.50-3.58 (m, 2H), 2.14-2.77 (m, 6H), 1.75(s, 3H)

Referential Production Example 17

0.5 g of methyl5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoatewas dissolved to 50 ml of methanol, added with an aqueous solution ofpotassium hydroxide (a mixed solution of 0.4 g of potassium hydroxideand 5 ml of water) at room temperature, and then stirred at the sametemperature for 1 day. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure to obtain 0.48 g of5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoicacid given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.95-4.01 (m, 1H), 3.50-3.56 (m, 2H),2.22-2.75 (m, 6H)

Referential Production Example 18

0.9 g of methyl2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoatewas dissolved to 50 ml of methanol, added with an aqueous solution ofpotassium hydroxide (a mixed solution of 0.7 g of potassium hydroxideand 5 ml of water) at room temperature, and then stirred at the sametemperature for 1 day. The reaction mixture was added with 10%hydrochloric acid, followed by extraction with ethyl acetate. Theorganic layer was washed with saturated aqueous solution of sodiumchloride, dried over anhydrous magnesium sulfate, and then concentratedunder reduced pressure to obtain 0.78 g of2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoicacid given by the below formula:

¹H-NMR (CDCl₃, TMS): δ (ppm) 3.50-3.59 (m, 2H), 2.16-2.75 (m, 6H), 75(s, 3H)

Formulation Examples are exemplified below. In addition, “part” meanspart by weight.

Formulation Example 1

9 parts of each of the present compounds (1) to (103) are dissolved in37.5 parts of xylene and 37.5 parts of N,N-dimethylformamide, and 10parts of polyoxyethylene styryl phenyl ether and 6 parts of calciumdodecylbenzenesulfonate are added thereto, followed by stirring andmixing well, to give an emulsifiable concentrate for each compound.

Formulation Example 2

To 40 parts of each of the present compounds (1) to (103) are added 5parts of SORPOL 5060 (registered trade name for TOHO KAGAKU KOGYO),followed by mixing well. To the mixture are added 32 parts of CARPLEX#80 (registered trade name for SHIONOGI & Co., synthetic hydratedsilicone oxide fine powder) and 23 parts of 300 mesh diatomaceous earth,followed by mixing with a juice mixer, to give a wettable powder foreach compound.

Formulation Example 3

To 3 parts of each of the present compounds (1) to (103) are added 5parts of synthetic hydrated silicon oxide fine powder, 5 parts of sodiumdodecylbenzenesulfonate, 30 parts of bentonite, and 57 parts of clay,followed by stirring and mixing well. Then an appropriate amount ofwater is added to this mixture, followed by further stirring,granulating with a granulator, and air drying, to give a granule foreach compound.

Formulation Example 4

4.5 parts of each of the present compounds (1) to (103), 1 part ofsynthetic hydrated silicon oxide fine powder, 1 part of Doriresu B(Sankyo Co., Ltd.) as a flocculant and 7 parts of clay are well mixedwith a mortar, followed by stirring and mixing with a juice mixer. Tothe resulting mixture are added 86.5 parts of cut clay, followed bystirring and mixing well, to give a dust for each compound.

Formulation Example 5

10 parts of each of the present compounds (1) to (103), 35 parts ofwhite carbon containing 50 parts of polyoxyethylene alkyl ether sulfateammonium salt and 55 parts of water are mixed and pulverized by the wetgrinding method to give a formulation for each compound.

Formulation Example 6

0.5 parts of each of the present compounds (1) to (103) are dissolved in10 parts of dichloromethane, and the resulting solution is mixed with89.5 parts of Iso-Par M (isoparaffine: registered trade name for EXXONCHEMICAL LTD) to give an oil solution.

Formulation Example 7

0.1 parts of each of the present compounds (1) to (103) and 49.9 partsof NEO-CHIOZOL (CHUO KASEI Co., LTD) are charged into aerosol can, andaerosol valve is fixed to the can. Then 25 parts of dimethyl ether and25 parts of LPG are filled in the can, followed and fitting an actuatoron it, to give an oil aerosol.

Formulation Example 8

0.6 parts of each of the present compounds (1) to (103), 0.01 parts ofBHT, 5 parts of xylene, 3.39 parts of deodorized kerosene and 1 part ofemulsifier [Atmos 300 (registered trade name for ATMOS CHEMICAL LTD)]are mixed and dissolved. The solution obtained and 50 parts of distilledwater are charged into aerosol container, and a valve is fixed to thecontainer. 40 Parts of propellant (LPG) are charged under pressurethrough the valve to give an aqueous aerosol.

The following test example will demonstrate that the present compoundsare useful as an active ingredient of noxious arthropod controllingagent.

Test Example 1

The formulation obtained in Formulation Example 5 using the presentcompounds (1), (2), (3), (4), (5), (6), (8), (9), (11), (12), (13),(14), (15), (16), (17), (18), (20), (21), (22), (23), (24), (25), (26),(27), (29), (30), (31), (32), (33), (34), (35), (36), (37), (38), (39),(40), (41), (44), (45), (46), (47), (48), (49), (50), (52), (53), (55),(56), (57), (58), (59), (60), (61), (63), (64), (65), (67), (68), (71),(72), (73), (74), (75), (78), (79), (80), (81), (82), (83), (84), (86),(87), (88), (89), (90), (91), (93), (94), (96), (97), (100), (101),(102) and (103) respectively, was diluted with water so that the activeingredient concentration came to 55.6 ppm to prepare a test solution.

50 g of molding Bonsoru 2 (available from Sumitomo Chemical Co., Ltd.)was put into a polyethylene cup having five holes of 5 mm in diameter,and 10 to 15 seeds of rice were planted in the polyethylene cup. Therice plants were grown until the second foliage leaves developed andthen treated with the test solution, which had been prepared asdescribed above and was absorbed in a volume of 45 ml from the bottom ofthe cup. The rice plants were left in a greenhouse at 25° C. for 6 daysand then cut into the same height of 5 cm. Thirty first-instar larvae ofbrown planthoppers (Nilaparvata lugens) were set free on the riceplants, which were then left in the greenhouse at 25° C. On the 6th dayafter the release of brown planthopper larvae, the number of brownplanthoppers parasitic on the rice plants was examined. As a result, inthe treatment with each of the present compounds (1), (2), (3), (4),(5), (6), (8), (9), (11), (12), (13), (14), (15), (16), (17), (18),(20), (21), (22), (23), (24), (25), (26), (27), (29), (30), (31), (32),(33), (34), (35), (36), (37), (38), (39), (40), (41), (44), (45), (46),(47), (48), (49), (50), (52), (53), (55), (56), (57), (58), (59), (60),(61), (63), (64), (65), (67), (68), (71), (72), (73), (74), (75), (78),(79), (80), (81), (82), (83), (84), (86), (87), (88), (89), (90), (91),(93), (94), (96), (97), (100), (101), (102) and (103),the number of parasitic insects on the 6th day after the treatment wasnot greater than 3.

Test Example 2

The formulation obtained according to Formulation Example 5 using thepresent compounds (1), (2), (3), (4), (5), (6), (8), (9), (10), (11),(12), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22), (23),(25), (26), (28), (29), (30), (31), (32), (33), (34), (35), (36), (37),(38), (39), (40), (41), (43), (44), (45), (46), (47), (48), (49), (50),(52), (53), (55), (56), (57), (58), (59), (60), (61), (63), (64), (65),(66), (67), (68), (69), (78), (71), (72), (73), (74), (75), (78), (79),(80), (81), (82), (84), (86), (87), (88), (89), (90), (91), (93), (94),(95), (96), (97), (99), (100), (101), (102) and (103) respectively, wasdiluted with water so that the active ingredient concentration came to500 ppm to prepare a test solution.

On the bottom of a polyethylene cup having a diameter of 5.5 cm, afilter paper having the same diameter was laid, and 0.7 ml of the abovetest solution was added dropwise on the filter paper, followed byputting 30 mg of sucrose on it uniformly as a bait. Ten female Muscadomestica imagoes were set free in the polyethylene cup and covered itwith a lid. After 24 hours, the number of surviving and dead Muscadomestica was examined and the rate of dead pests was calculated.

As a result, in the treatment with each of the present compounds (1),(2), (3), (4), (5), (6), (8), (9), (10), (11), (12), (13), (14), (15),(16), (17), (18), (19), (20), (21), (22), (23), (25), (26), (28), (29),(30), (31), (32), (33), (34), (35), (36), (37), (38), (39), (40), (41)(43), (44), (45), (46), (47), (48), (49), (50), (52), (53), (55), (56),(57), (58), (59), (60), (61), (63), (64), (65) (66), (67), (68), (69),(70), (71), (72), (73), (74), (75), (78), (79), (80), (81), (82), (84),(86), (87), (88), (89), (90), (91), (93), (94), (95), (96), (97), (99),(100), (101), (102) and (103), the rate of dead pests was 70% or more.

Test Example 3

The formulation obtained according to Formulation Example 5 using thepresent compounds (1), (2), (3), (4), (5), (6), (7), (8), (9), (10),(11), (12), (13), (14), (15), (16), (17), (20), (21), (23), (26), (29),(30), (31), (32)_(r) (33), (34), (35), (36), (37), (38), (39), (40),(41), (44), (45), (46), (47), (49), (50), (52), (53), (55), (56), (57),(58), (59), (60), (61), (63), (64), (65), (67), (68), (69), (70), (71),(72), (73), (74), (75), (78), (79), (80), (81), (84), (86), (87), (88),(89), (90), (91), (93), (94), (96), (97), (100), (101), (102) and (103)respectively, was diluted with water so that the active ingredientconcentration came to 500 ppm to prepare a test solution.

On the bottom of a polyethylene cup having a diameter of 5.5 cm, afilter paper having the same diameter was laid, and 0.7 ml of the abovetest solution was added dropwise on the filter paper, followed byputting 30 mg of sucrose on it uniformly as a bait. Two male Blattellagermanica imagoes were set free in the polyethylene cup and covered itwith a lid. After 6 days, the number of surviving and dead Blattellagermanica was examined and the rate of dead pests was calculated.

As a result, in the treatment with each of the present compounds (1),(2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14),(15), (16), (17), (20), (21), (23), (26), (29), (30), (31), (32), (33),(34), (35), (36), (37), (38), (39), (40), (41), (44), (45), (46), (47),(49), (50), (52), (53), (55), (56), (57), (58), (59), (60), (61), (63),(64), (65), (67), (68), (69), (70), (71), (72), (73), (74), (75), (78),(79), (80), (81), (84), (86), (87), (88), (89), (90), (91), (93), (94),(96), (97), (100), (101), (102) and (103) the rate of dead pests was100%.

Test Example 4

The formulation obtained according to Formulation Example 5 using thepresent compounds (1), (2), (3), (4), (5), (6), (7), (8), (9), (10),(11), (12), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22),(23), (24), (25), (26), (29)_(r) (30), (31), (32), (33), (34), (35),(36), (37), (38), (39), (40), (41), (42) (45), (46), (47), (49), (50),(51), (52), (53), (56), (57), (58), (59), (60), (61), (63), (65), (67),(68), (69), (70), (71), (72), (73), (74), (75), (76), (78), (79), (80),(81), (82), (83), (84), (86), (87), (88), (89), (90), (91), (92), (93),(94), (95), (96), (97), (100), (102) and (103) respectively, was dilutedwith water so that the active ingredient concentration came to 500 ppmto prepare a test solution.

0.7 ml of above test solution was added to 100 ml of ion exchanged water(active ingredient concentration: 3.5 ppm). Twenty last-instar larvae ofCulex pipiens pallens were set free in the solution. After one day, thenumber of surviving and dead Culex pipiens pallens was examined and therate of dead pests was calculated.

As a result, in the treatment with each of the present compounds (1),(2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14),(15), (16), (17), (18), (19), (20), (21), (22), (23), (24), (25), (26),(29), (30), (31), (32), (33), (34), (35), (36), (37), (38), (39), (40),(41), (42), (45), (46), (47), (49), (50), (51), (52), (53), (56), (57),(58), (59), (60), (61), (63), (65), (67), (68), (69), (70), (71), (72),(73), (74), (75), (76), (78), (79), (80), (81), (82), (83), (84), (86),(87), (88), (89), (90), (91), (92), (93), (94), (95), (96), (97), (100),(102) and (103), the rate of dead pests was not less than 90%.

INDUSTRIAL APPLICABILITY

The present compounds are useful for an active ingredient of noxiousarthropod agent.

1. An organic sulfur compound given by the formula [I]:

wherein R¹ represents a C3-C6 fluoroalkyl group, R² represents a cyanogroup, a group represented by C(═O)R⁵ or a group represented by C(═S)R⁶,R³ represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group, R⁴represents a C1-C5 fluoroalkyl group, R⁵ and R⁶ independently representa C1-C4 alkoxy group, an amino group optionally substituted by one ortwo C1-C4 alkyl group(s) or a C2-C5 cyclic amino group, n represents 0,1 or
 2. 2. The organic sulfur compound according to claim 1, wherein nis
 2. 3. The organic sulfur compound according to claim 1, wherein R² isa cyano group or a group represented by C(═O)R⁵.
 4. The organic sulfurcompound according to claim 1, wherein R² is a cyano group.
 5. Theorganic sulfur compound according to claim 1, wherein R² is a grouprepresented by C(═O)R⁵ and R⁵ is an amino group optionally substitutedby one or two C1-C4 alkyl group(s).
 6. The organic sulfur compoundaccording to claim 1, wherein R² is a group represented by C(═O)R⁵ andR⁵ is an amino group.
 7. The organic sulfur compound according to claim1, wherein R³ is a halogen atom.
 8. A noxious arthropod controllingagent comprising the organic sulfur compound according to claim 1 and aninert carrier.
 9. A method for controlling noxious arthropods applyingan effective amount of the organic sulfur compound according to claim 1to noxious arthropods or at a habitat of noxious arthropods.
 10. Use ofthe compound according to claim 1 for noxious arthropod control.
 11. Anorganic sulfur compound given by the formula (d):

Wherein R² represents a cyano group, a group represented by C(═O)R⁵ or agroup represented by C(═S)R⁶, R³⁻² represents a hydrogen atom or a C1-C4alkyl group, R⁴ represents a C1-C5 fluoroalkyl group, R⁵ and R⁶independently represent a C1-C4 alkoxy group, an amino group optionallysubstituted by one or two C1-C4 alkyl group(s) or a C2-C5 cyclic aminogroup and n represents 0, 1 or 2.